


(Not Too Sure) But I Know That It’s Meant to Be

by Aerica_Menai



Series: 21st Century Destiel [1]
Category: Supernatural
Genre: (between Dean/OMC), Alternate Universe - College/University, Asexual Castiel (Supernatural), Asexual Character, Asexuality, Asexuality Spectrum, Bad BDSM Etiquette, Bi!Dean, Dean Winchester Has a Panty Kink, Dubious Consent, Feminization, Fluff, Hurt/Comfort, John Winchester's A+ Parenting, Kink Negotiation, M/M, Mild Sexual Content, OMC is based on Lee Webb from S15E7, ace!cas, ace!sam, all-human AU, and husbanding, brief mentions of John Winchester being an eliminationist queer phobic asshole, but Cas is worried in the meantime), lots of pop culture references, perceived stalking of Cas by Dean (unintended and in the end harmless
Language: English
Status: Completed
Published: 2020-10-02
Updated: 2020-10-02
Packaged: 2021-03-07 21:14:40
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 18
Words: 34,307
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26774233
Author URL: https://archiveofourown.org/users/Aerica_Menai/pseuds/Aerica_Menai
Summary: Dean was just hoping to get his brother someone to talk to about being ace; somehow that turns into him gaining a new friend, and then a boyfriend. (Also, Dean wears panties.)
Relationships: Bobby Singer & Mary Winchester, Castiel & Sam Winchester, Castiel/Dean Winchester, minor Sam Winchester/Sarah Blake - Relationship, past Dean Winchester/OMC
Series: 21st Century Destiel [1]
Series URL: https://archiveofourown.org/series/1951873
Comments: 1
Kudos: 65
Collections: Asexual Supernatural Mini Bang 2020





	1. Castiel I

**Author's Note:**

> Phew. I think I got all the tags and warnings up there - quite a few more than usual this time!
> 
> This is my entry for Asexual Supernatural Mini-Bang 2020, which ended up growing far larger than planned - and even spawned a sequel, which I will be posting next month.
> 
> Major thanks to the mod(s) of the bang, my fantastic artist Severepaperdragon (whose AMAZING art can be found here: https://severepaperdragon.tumblr.com/post/630893094632636416/art-masterpost-not-too-sure-but-i-know-that), and my amazing betas grayraincurtain and bellatemple who made sure this fic ended up happening at all; can't thank you enough <3 
> 
> Rated M for mild sexual content, to be safe - it is contained in one chapter and will be easily skippable, if you prefer; title from 21st Century by the Red Hot Chili Peppers

Castiel Adler was a little worried about attending his first meeting of his college’s Gender and Sexuality Alliance. Asexuality was not always easily accepted – even in places like this, as his internet explorations had taught him – but he had promised himself that he would at least give it a try.

And to his surprise, quite a mixed crowd attended. Even someone he could have sworn was straight, with the swagger and all the flirting, but…Castiel shook his head. It didn’t matter – Castiel was not here to judge. He was quickly distracted by the dark-haired woman who barreled up to him. 

“Hi, you must be new, never seen you around before. I’m Meg. And you are?” She gave him a very thorough once-over, licking her lips. Castiel shuddered a bit, thrusting his hand out to shake. “Hi, I’m Castiel. And I’m asexual, not looking for anything right now,” he blurted out as she took his hand. 

“Shame,” she tsked but – to her credit – stopped with the eye-fucking and immediately Castiel felt far more comfortable in her presence. “And…I’m sorry, what did you say your name was?”

“Castiel. The Angel of Thursday,” he explained with a sigh at her blank stare. 

“Named after an angel, even if it’s one of the harder ones to pronounce,” she chuckled, before her eyes lit up. “Ooh. Ever seen It’s a Wonderful Life?”

“No?” Castiel replied questioningly.

“Stars an angel with a much more pronounceable name, and it’s also your nickname from now on, Clarence,” she continued gleefully.

Castiel sighed. “If you insist.”

“Indeed I do! Come on, sit next to me, they’re going to call the meeting to order soon. You look like you’ll need a guiding hand, and I’ve been coming for a while.”

“Is it that obvious I’m new?” he asked as they sat down.

“Definitely, Clarence. All you freshpeople stick out – we’re a close-knit bunch. One new person is rare enough – a whole group? You all stick out, and we all try to gather you under a friendly wing ASAP.” She winked at him.

Castiel smiled back. “Thank you, I appreciate it.”

Someone Castiel assumed to be the head of the club called everyone to attention before he and Meg could continue their conversation. “Alright all, welcome to the first Gender and Sexuality Alliance meeting of the year – although you’re far more likely to hear us call it the GSA. My name is Wren, I go by they/them pronouns. We’ve got a big group this time, so we’re going to start by going around and introducing ourselves – let’s start with name, year, pronouns, major and orientation, if you feel comfortable telling us. No pressure either way. Let’s start with you, to my right.”

Castiel was surprised at the variety of identities that were slowly revealed in the group of at least a hundred students, probably more. He did notice that the possibly-straight student who had caught his attention at the beginning declined to state his orientation, but soon enough it was his turn, and while he was nervous, he hadn’t come all this way for nothing. “Hi, my name is Castiel, he/him, first year, no major yet and…” He took a deep breath. “I’m asexual.”

Possibly-Straight Student snapped to attention at that, and stared at him on and off for the rest of the meeting. When the meeting was wrapping up, Castiel noticed that P.S.S. was slowly heading his way. “Meg – I should probably get going,” he said, slowly backing away even as he tried to be subtle about it. 

“Clarence, why – ” Meg frowned as she also clocked P.S.S. heading their way. “Is he bothering you?”

Castiel hesitated before nodding. 

Meg was all business. “You get out of here, I’ve got this.”

“Thank you,” Castiel breathed before fleeing. The last thing he wanted was any sort of…incident over his identity. 

*~*

Meg had found him later and let him know that the other student – Dean, apparently – had been pretty insistent about finding Castiel, even if he wouldn’t tell Meg why. “I will say, Clarence, he didn’t strike me as the type to be afraid of. Charlie’s the one who scooped him up, and she’s usually a good judge of character. Maybe just talk to him?”

Castiel nodded but internally decided not to give Dean the chance to ask his question. Surely it couldn’t be that hard to avoid one student in a school of over 10,000?

And for the first few days, it worked. Castiel went to classes, had lunch with friends (perhaps they were more like acquaintances, at this point, but so early in the year Castiel would take what he could), did his homework and generally led a peaceful existence. 

But then, during one of his library study sessions, Castiel noticed there was somebody hovering in his general area. He looked up to see – Dean? How – ?

Dean opened his mouth, looking – surprisingly nervous – but Castiel held up a hand, pointed at his large stack of books, and made a shooing motion. 

Dean frowned and opened his mouth again, but Castiel merely scowled back and made the shooing motion more firmly this time. Whatever Dean wanted to say, it would have to wait. 

Dean held up his hands in surrender and left; but somehow Castiel knew this wouldn’t be the end of it. 

Soon Meg and other friends of his started telling Castiel that they had been – interrogated, was the word most of them used – by one Dean Winchester. Asking about Castiel’s habits and personality and interests and...all sorts of things that made Castiel more and more nervous about Dean’s intentions. 

Even Meg was starting to get worried after a couple weeks of this. “Alright Clarence, this…this is getting weird. I’m talking to Charlie about this ASAP, but until then – don’t go anywhere alone, okay? You don’t want to end up facing this guy by yourself, alright? Promise me.”

In the moment, Castiel did – and meant it, but he forgot about how he was usually the last person kicked out of the library when they closed on Fridays and he was usually the only person left awake on campus for those stumbling home walks. Usually, that is; tonight, one Dean Winchester had decided to show up, and Castiel let his fatigue and annoyance get the better of him.

He groaned loudly. “Really? You? Now?”

Dean grimaced. “I know. But dude, this is the first time you’ve been by yourself all week. What’s up with that, anyway?”

Castiel stared at him. “They’ve been worried about the guy stalking me!” The “you idiot” ending to the sentence was strongly implied. 

Not that Dean seemed to notice as he frowned. “Who the hell has been stalking you?”

Castiel raised an eyebrow.

Dean stared back for a second before it seemed to click, and he flushed. “Me?? But I’m not – I just – ” He groaned. “I just want your phone number,” he finally mumbled.

Castiel sighed. “Why? I’m not interested in dating right now.”

Dean flushed even darker and rubbed a hand through his hair. “I’m not – this isn’t about – you’re cute but – argh!”

Castiel couldn’t help it; he burst out laughing. The creepy mental image he had of Dean melted away in the face of this – this absolute *dork* who couldn’t even finish a sentence. 

Dean grumbled a little, but Castiel could see he was smiling as his own laughter petered out.

“I guess I kinda deserved that.” He sighed. “Look, honest truth? My little brother, he figured out he was ace recently, but he’s a sophomore in high school and...it’s been rough for him. I just...you're the only other ace person I know, and I thought...I thought you might be able to help him. You know, if you don't mind, of course." Dean finished quickly. 

“*That’s* what you’ve been stalking me for weeks over??” Castiel exclaimed incredulously.

“It wasn't stalking! Just...recon. I can't let just anybody near my little brother." Dean retorted. 

Castiel put his head in his hands. Maybe he was tired, maybe he was just a soft touch, but he found himself deciding to agree to talk to Dean’s little brother about being ace in high school, which – oof. Whether you knew or not, being ace in high school was not easy and Castiel figured that even if he wasn’t certain he would be all that helpful, at least the kid would have someone to talk with who got it.

That being said, Castiel was still a little pissed at Dean and was not going to make this as easy as Dean seemed to have thought it would go. “Okay, Dean, I’ll talk to your brother – but I want his phone number, I’ll contact him directly,” Castiel said firmly.

Dean balked a little. “But – ” 

“Did you uncover anything in your ‘recon’ that makes you worry I’ll misuse the phone number?” Castiel interrupted. 

“No...” Dean admitted.

“You, on the other hand, have proven yourself to be underhanded and sneaky and who knows what you would do with my phone number. Ergo, you’re not getting my phone number, but I’m happy to take your brother’s.”

Dean groaned. “Fine! Fine.” He pulled out a scrap piece of paper from his pocket, took the pen Castiel offered him and scribbled down the information.

But when Castiel checked the paper, there wasn’t one but two phone numbers – one labeled with an S, one labeled with a D.

“My brother’s name is Sam, that’s his phone number. And if there’s anything you want to ask me, or anything you think I should know about Sam, that’s my phone number.” Dean held up a hand before Castiel could say anything. “You don’t have to use it if you really don’t want to, but...just in case. For my peace of mind?”

Castiel groaned but entered both phone numbers into his phone. “Done. Can I go home now?”

“Oh, yeah man, I’m sorry, I forgot how late it was.” Dean seemed to take a closer look at Castiel. “...You don’t look so steady there.”

“I’m FINE!” Castiel protested loudly before starting to walk toward his dorm, gait admittedly more wobbly than he’d like.

Dean caught up quickly. “Fair enough. But since my dorm’s the same direction, I’m just going to make sure you get there safely, alright?”

Castiel glared at him blearily, the adrenaline rush from Dean showing up and scaring him fading. “You’re my stalker, should I really be showing you where I live?”

Dean chuckled. “I’m not a stalker anymore, we’ve introduced ourselves and you’re about to make friends with my brother – because Sammy always manages to make friends – which means that I’m very logically taking care of Sammy’s friend-to-be, and knowing where you live is not going to be used for anything other than knowing you got home safe, okay?”

“Too many words,” Castiel grumbled back.

Dean laughed loudly at that. “Okay, okay. I just wanna know you’ll be alive to talk to Sammy later.”

“Fiiiiiiiiine,” Castiel sighed (not whined, of course not; he may have been tired but he still had his dignity). Dean just grinned and stuck to Castiel like – like – like a sticky thing, nudging him here and there to stop him from tilting too far one way or crashing into any obstacles. Finally, Castiel arrived at his dorm safely and got inside, but he grabbed the door before it could swing shut. “And – and you? Where’s your dorm?”

Dean ruffled a hand through his hair. “Not that far,” he replied unconvincingly.

Castiel blinked at him. “You’re lying, and now I’m going to be worrying about you.” He sighed before holding out a hand, gesturing for Dean to come closer. “Gimme your phone.”

Dean came close enough for Castiel to almost reach the phone in his outstretched hand. “...Are you sure?”

“I won’t be able to sleep if I’m worrying about you, so you damn well better not forget to text me when you’re back in your dorm,” Castiel snapped before motioning for the phone again. 

Dean handed it over and watched as Castiel typed in his information. 

“Alright, done.” And then Castiel gave Dean a glare that was startling in its intensity. “Do not even think about abusing this privilege, Dean, or I will make you regret it.” 

Dean held his hands up in surrender. “Wouldn’t dream of it. G’night, Cas!”

“You haven’t earned nickname privileges yet!” Castiel yelled back, mouth moving before his brain registered what was being said.

“G’night Castiel!” Dean responded before going on his way.

Castiel sighed to himself as he started up the stairs. What had he gotten himself into?


	2. Dean I

Dean Winchester was not looking forward to attending his first GSA meeting. But he had promised both Sammy, his pain-in-the-ass-“it’ll-be-good-for-you-Dean” little brother, and Charlie, his crazy and amazing new friend from the engineering department. Charlie had been president of her high school’s GSA, so she was excited; Dean, on the other hand, had only recently come out of the closet – if it even counted if you were only out to your brother, one friend and an ex? 

Whatever, Dean was bi, but...both inside and outside the community, that wasn’t always accepted. So Charlie had promised him that she would be there for his first meeting, to act as a buffer. Of course, instead, Dean’s luck struck again – right as they were heading to the meeting room, Charlie dropped an M&M. Down her shirt. She glanced apologetically at Dean but he waved her on towards the bathroom; nobody needed or deserved chocolate stains inside their clothes. He could handle a few minutes by himself. He had this.

*~*

Dean underestimated either the level of his nerves or the strength of his past habits but all too quickly he found himself slipping back into what Sammy called his “machismo bullshit” – strutting around as though he owned the place, flirting with everyone (female) that met his eye and generally being a bit of a dick. 

He never pushed anyone’s boundaries, accepting brush-offs as easily as more positive responses (because neither his mother nor Charlie would stand for anything less) but he could feel some judgmental stares from around the room, which – understandable. 

Still couldn’t stop himself from doing it though. Not until Charlie showed back up and smacked his arm. “Really Winchester?? I was gone for what – ten minutes?”

Dean growled at her halfheartedly. They both knew she was right, that Dean was being ridiculous. Before Dean could say anything else, Charlie just sighed. “Come on, let’s go meet some people. No one’s going to bite.” 

And indeed, by the time the president called the meeting to order, Dean had to admit he was glad he had come. He had met some of Charlie’s other friends and even been invited to join their next D&D campaign. He had never played before, but if Charlie had gotten so excited about it, he had to at least see what all the fuss was about. 

He was lost in thought when he suddenly heard someone say, “ – and I’m asexual.”

Dean immediately snapped to attention, staring at the guy defiantly glaring around the room, as though waiting for someone to say something. When no one did, he smiled brightly and sat back, tension bleeding out of his posture.

And Dean…Dean’s mind was racing. He was ace, like Sammy. Sammy was worried about dealing with being ace in high school. This guy could help. Dean had a mission now: find out if this guy was someone his little brother should be talking to in the first place and, if so, get him in contact with Sammy.

*~*

Castiel was...not who he had expected. Of course, being tired could have been a large part of it...but Dean hadn’t expected to be called a stalker nor actually get Cas’ number after the fuss the guy had put up about giving it to him. And just to make sure Dean got home safely? That was...surprisingly thoughtful. Something Sammy would do.

Speaking of, Dean pulled out his phone to give Sammy the good news. 

His brother was (predictably) horrified that Dean had basically stalked Castiel, even as he thanked Dean for finding him someone to talk to. ‘Not that talking to Dean wasn’t helpful and great,’ he quickly added in another text, ‘but...it would help to talk to someone who got it.’

Dean smiled when he got those texts; he knew that he alone wasn’t enough for his brother, but he was glad he had found someone else better.

*~*

As it turned out, Castiel and Sam hit it off majorly; both history nerds with bleeding hearts and a snarky sense of humor. Castiel had an underdeveloped understanding of pop culture that Sam immediately enlisted Dean in helping him change, so Dean and Castiel started spending a lot of time outside class together. 

And after a couple months...it wasn’t that Dean and Cas (he had finally allowed the nickname after a couple weeks) weren’t friends. They spent a lot of time together, had inside jokes, were starting to learn quite a bit about each other – but...they also didn’t spend much time together with other people. It was always just them and whatever movie or TV show Dean had decided was next. Sometimes they brought food, but they never ate together in the cafeteria or hung out at GSA meetings; Dean never invited Cas to play D&D with Charlie’s group, as much as he was starting to suspect that Cas would love it. 

It was almost like Cas was a dirty secret he was hiding from everyone besides Sam, which wasn’t true, or at least, shouldn’t have been, but every time he tried to talk to Charlie about Cas...the words just wouldn’t come out. His time spent with Cas was still something only he and his brother knew, even if Dean’s entire friend group was starting to suspect and/or tease that Dean was secretly dating someone. (Which...of course Dean wasn’t. That would be crazy. No matter how cute, and smart, and funny, and amazing Dean found Cas...no.)

Then Cas spilled the beans on Sammy.

*~*

“So, Dean,” Cas asked distractedly as Dean cued up Grease, “I forgot to ask earlier, but are you planning to come with me next week?”

Dean turned around. “...Come with you where?”

Cas stilled. “...Did Sam not tell you?”

Dean frowned as he stalked a couple steps closer. “Tell me what?”

Cas swallowed. “I’m going over to your house to meet Sam properly?”

Dean’s jaw dropped. Sammy was freaking trying to get one over on him, getting Cas to come over without letting Dean know! Too bad, bitch, Cas was too good of a friend for that to happen.

“I am definitely coming,” Dean gritted out as he sent Sam multiple texts about what a dirty traitor he was, how Dean would get his revenge and would see him next week, bitch.

Cas’ phone dinged soon after, and he frowned at what he read there. “Oh, I wasn’t supposed to tell you.”

“I bet not,” Dean grumbled as he sent another text telling Sam to back off, Cas had accidentally told him and he didn’t need Sam making Cas feel guilty – it was done, he was coming, end of story. A lightbulb went off as he was typing and he sent one last text: ‘How were you even going to explain how you knew Cas without Cas and I being friends first? Mom and Bobby don’t know about you being ace.’

Dean chuckled victoriously at Sam’s reply text: ‘You’re such a jerk.’ Sammy knew he was right and just didn’t want to admit it, such a sore loser.

“Don’t worry about it Cas, I have to be there anyway,” Dean explains. “Mom and Bobby don’t know Sam’s ace, so there’s no other reason for you two to have met other than me introducing you.”

Cas blinked at him. “You call your father by his name?”

Dean chuckled. “No, no, Bobby’s a good friend of my mom’s – he’s basically my uncle. He lives just down the street, but he’s over a lot because he gets lonely puttering around in his house by himself. Not that you heard that from me,” Dean finished quickly.

Cas just nodded, then raised an eyebrow. “You said that there’s no reason for Sam and I to have met other than you introducing us…but that’s what you did.”

“I mean, technically yes, but – dammit Cas, the story is that we were friends and then I introduced you two because you’re both history nerds, alright?”

“Seems a little thin, but alright,” Cas shrugged.

*~*

When Dean and Cas arrived at Dean’s house, and his mom asked how Sam and Cas met, Dean barreled in with the same story he had explained to Cas – with a little more to it, as Cas had suggested, but Dean’s original explanation was the bare bones of it. His mother accepted it completely, but Dean could have sworn he saw Bobby raise an eyebrow at both him and Cas for just a second before the expression disappeared. 

In any case, Cas was a very welcome house guest. It was rare for Sam and Dean to agree on friends – Dean’s friend from his senior year, the one he apparently spent most of his time with, was someone Sam *hated* – so Mary and Bobby were very pleasantly surprised to see all three boys getting along so well. 

Oh sure, there was plenty of bickering and glares and suspicious thumping noises, but none of it ever festered, became something darker as it could between the Winchester brothers. It was surface level tension, nothing deeper, and Mary made sure that both her boys and Cas knew that Cas was welcome under her roof anytime, Dean or no Dean, Sam or no Sam. (Cas had been skittish enough at any mention of his family or his home life that Mary wanted to make sure he knew that he had a home with them now.)

Cas flushed and thanked her quietly. Dean had disappeared, so Sam took Cas aside to spend a few more minutes with him sans his annoying older brother.

And where was Dean? Bobby had pulled him aside and was trying to humiliate him to death with one simple question. “You two boys are being safe, right?”

At first, Dean didn’t get it. “Of course we’ve been driving safe, Bobby, you know me better than that!”

Bobby just snorted. “That ain’t what I meant.”

Dean just stared blankly until Bobby groaned and took off his trucker cap, rubbing a hand over the top of his head. “I was hoping I wouldn’t have to do this,” he muttered tiredly before pulling a handful of – 

Dean immediately recoiled. “Bobby! We’re just friends, okay? No need for any of – those!”

Bobby raised an eyebrow. “Like you were ‘just friends’ with Lee?”

The blood drained from Dean’s face. “I – uh – ” He buried his face in his hands. “I-never-actually-slept-with-Lee-and-I-have-no-intention-of-sleeping-with-anyone-anytime-soon-so-please-put-those-away,” Dean replied as quickly as he could.

Bobby squinted at him for a second before sighing. “Fair enough. Still, had to buy ‘em, so you have to take ‘em.”

Dean opened his mouth to reply but quickly shut it at Bobby’s stink-eye, huffily pocketing the condoms and fleeing the scene. 

“See you soon, boy,” Bobby called after him.

“Yep-love-you-bye,” drifted back at Bobby, who chuckled. He didn’t know who that boy thought he was fooling – he was obvious when he was panting after Lee, even before Bobby had seen them making out in his garage. Now, Dean was showing similar signs with Cas, but for some reason, he seemed more reluctant to accept his feelings this time around. Maybe Sam would have some insight...

*~*

Dean was so intent on getting away from Bobby and the memories of Lee that he nearly ran Cas over. 

“Dean? Are you alright? You look – ” 

“I’m fine, promise,” Dean interrupted. “Would you be okay driving us back to campus? I’m...really tired.”

By this point Sam had drifted up behind Cas, and frowned at Dean. “You’re voluntarily giving up the chance to drive? That’s more than just you being tired, Dean, what’s – ” 

“I’m fine, Sam, god,” Dean snapped. Sam blanched as the tone of voice registered, shrinking in on himself a little.

“Shit, Sammy, no, I – I’m sorry. Just...did you know that Bobby knew about me and Lee?”

Sam shook his head.

Dean dug his fingers into his hair. “Apparently he not only knows, he’s known for a while and – even though he’s fine with it, and that’s good, now – ” Dean gritted out before stopping himself.

Cas stepped forward softly. “I can go wait in the car, if you give me the keys?”

Dean immediately threw his keys at Cas. Cas huffed when they hit the floor and he had to bend down to pick them up (“handing people things instead of throwing them at them, Dean, it’s not that hard,” he’d told Dean more than once before) but he didn’t say a word as he walked off.

Sam gave Dean a hard hug. “I know Lee leaving messed you up, and you didn’t want to talk about it, but – Dean. I’m here, Bobby’s here – hell, I bet even Charlie and Cas would listen. You can’t keep holding it in like this.”

Dean hugged him back, forcing a smile. “I’ll text you later, Sammy,” was all he said in response.

In the car, Dean closed his eyes and let the memories wash over him.


	3. Flashback I

**Summary for the Chapter:**

> This is the chapter that earned the M rating! The warnings about John Winchester, Lee Webb, Dean's panty/feminization kink and bad BDSM etiquette are in full effect; if any of that is worrying, there will be a (much less detailed) recap in another chapter - you do not need to read this to understand the rest of the fic. 
> 
> For those of you who are reading on...this is my first attempt at writing anything like this, so please keep that in mind >_<

The summer between Dean’s junior and senior year of high school was...turbulent, to say the least.

John had been called back to active duty, with no real idea when he’d be back, so Sam and Dean’s usual trip to spend the summer with their mom needed a lot more just-in-case packing. They had to make sure that if John didn’t make it back in time for Sam to start his last year of middle school and Dean his senior year of high school, they’d be prepared to start school in Sioux Falls. 

While Dean was in the middle of packing, John knocked on his door. “You got a minute?”

“Sure, Dad.” Dean straightened up. 

John clapped him on the shoulder. “I just wanted to let you know that you should really make the most of your summer in Sioux Falls this year.” 

Dean nodded silently, a confused look on his face.

John just chuckled. “Yeah – come hell or high water, I’m coming back by the end of your senior year and you and I will be making the trip out to the Naval Academy.”

Dean sucked in a breath. Right after high school ended? But – 

John frowned. “Would it kill you to show a little excitement? It wasn’t exactly easy to make sure they gave you a spot...”

Dean immediately forced an almost-natural smile onto his face. “Right, of course, thank you! I was just thinking about what else I should pack to make sure I’m the best prepared I can be.”

John grinned broadly and put both his large hands on Dean’s shoulders. “That’s my boy! I’ll leave you to it.”

*~*

Dean was in a daze for the next few days as he realized that his dad wasn’t going to let him have a say in his own future, that this was basically a done deal and there really wasn’t anything Dean could do to change it. He never really could stand up to his father – not for himself, anyway – and as much as he was dreading starting at the Naval Academy and all the expectations and pressures that would come with it, there was also a little, tiny bit of...relief. He wouldn’t have to worry about making choices when his dad was making them for him; no need to worry that he was making a mistake or doing something that would disappoint him. It wasn’t all bad.

Once Dean came to that conclusion, he started to pay more attention to what was going on around him and one thing immediately got his attention: Sammy was being squirrelly. Kid was hiding something, and not very well at that – he was lucky Mom wasn’t around enough to notice his tells and Bobby hated prying when he didn’t absolutely have to. 

So the next chance Dean got alone with Sammy, he took it. “Anything you want to talk to me about, Sammy?”

Sam shook his head, peering up at Dean nervously. And it broke Dean’s heart to think that his brother might be scared of him...the way they were both scared of their dad. Dean always swore he would never ever do that to Sammy, and now was a good time to put his money where his mouth was.

He knelt down eye-to-eye with his still-short little brother. “You don’t have to tell me now, if you’re really not ready,” he started quietly. “But Sammy, whatever you have to tell me – whatever you’re scared to tell me – I promise that no matter what it is, I will always be here for you. No matter what, okay?”

Sammy nodded, blinking back tears, before throwing his arms around Dean and burying his face in his neck. Dean hugged him back, eyes feeling a little misty himself.

*~*

A couple of days later, right as Dean was about to get into bed, Sammy showed up in his doorway. “Can I talk to you?” he mumbled, wringing his hands. 

“Of course,” Dean replied, sitting down on the bed and patting the space next to him. Sam sat, but – rigidly. Still tense, still worried about whatever he was going to say. 

Sam was quiet for a couple minutes before blurting, “Dean, I – I don’t think I’m straight.”

Dean immediately froze, a chill running down his spine. “Dad – Dad can’t ever know,” he forced out through numb lips. 

“I – I know,” Sam stuttered nervously. “But... I wanted you to know.” He turned to face Dean, eyes steely. “I’m asexual. It means I’m not sexually attracted to anyone. And no matter what Dad, idiots on the internet, or society might think, I am NOT a freak.” He deflated a little. “Not that I’m exactly ready to tell the world yet, but...” He glanced away, at the doorway, before turning back to face Dean. “I thought you should know. Because...Dad’s wrong.”

Dean stared back at Sam, mind whirring. As much as their dad had spewed his hatred of “unnatural” people and his belief that they all needed to be “fixed” or wiped out...Dean believed, deeper than anything else, that Sam? Sam was part of what was good in this world. And if Sam wasn’t straight, if he fell into John’s definition of “unnatural” – then John was wrong. It was that simple.

“Yeah,” Dean breathed. “Dad’s wrong.”

Sam peered up at him, a strange look in his eyes. “And…is there anything you want to tell me, Dean?”

Dean just raised an eyebrow. “Nope. Why?”

Sam just shrugged and looked away. “No reason. But…we’re good?”

“Of course, Sammy,” Dean promised, throwing an arm around his shoulders and pulling him into a tight half-hug. 

*~*

The week wore on and Dean grew even more worried about what the next year would hold. Now he not only had to worry about being shipped off to the Naval Academy – or defying his dad’s “my way or the highway” style of parenting – but what might happen to Sam after Dean left, whether for the Academy or just away from his father’s wrath. Sam wasn’t straight, and if his father found out? Absolutely nothing good could come of it, and for once Dean wouldn’t be there to protect him. 

But Dean tried to put it out of his mind, tried to focus on making the most of his last summer of freedom – going to the movies with Sammy, flirting with cute girls at the local hangouts, eating his body weight in pie and popsicles, swimming and laughing and helping his mom with dinner, Bobby grumbling in the background… 

Then, with only a couple weeks of summer left, the letter came. 

John had been sent on a mission that went to hell, and he, along with the rest of his unit, had died. 

Sam and Bobby and his mom were upset, of course, but Dean…all he could think about was how he had been so dreading John coming back, that a little part of him had wished that John would never come home, and now – now he never would. 

Dean sunk deeply into his grief and guilt, buried to the point that he felt like he would never escape it.

*~*

And if it wasn’t for Bobby, maybe he never would have. Sam’s logic and his mom’s attempts at understanding fell flat because – as much as they loved him and really tried to see where he was coming from, Dean was at a point where he just couldn’t explain anything properly and didn’t have the energy to try and meet his family halfway, no matter how much he needed to. Sam and Mary needed Dean to reach out to them to help him; Bobby came up with a different solution.

Rather than confront Dean directly, Bobby put him to work in his garage. Dean had always loved cars and had always had a basic knowledge of how to keep them running, so working in the garage was – well. Cathartic. To get his hands dirty, to feel and see his efforts making a difference in each car that got to drive off the lot after he worked on it, to lose himself in gears and oil and tools for hours at a time; it helped him immensely. Soon Dean had worked off enough of his anxiety and guilt that he could start talking to Sam and his mom like he needed to, not to mention start thinking about a possible career path to do with cars instead of guns.

So even once the school year started, Dean would put in hours at the garage for a little extra money or just to work off some steam that wasn’t otherwise being released.

*~*

Sammy going to middle school as a new eighth grader was a little strange, but Sam wasn’t the only new kid transferring into eighth grade, so at least he had the immediate makings of a friend as the two banded together. 

Dean, though – Dean was the only new incoming senior at the high school, so the administration thought a fellow student showing him around would be helpful. For some reason, they chose Lee Webb – captain of the hockey team and a troublemaker (even if his smile was usually enough to get him out of anything he landed in). 

He and Dean were soon thick as thieves. He was the reason Dean at least tried ice skating, even if said try went *horribly* – ending with Dean sprawled out on the ice, soaking wet, and having been in danger of losing his fingers a couple times. Instead, Lee introduced Dean to street hockey between his continued shifts at the garage (which Dean quickly picked up and enjoyed playing), and soon Lee was stopping by after hockey practice – sometimes for games, sometimes just to hang out.

One particularly rough tussle in the garage led to Lee pinning Dean on the floor, faces almost close enough to touch. Dean still didn’t know who had moved first, but all of a sudden they were kissing. After a pretty swoon-worthy kiss, if Dean said so himself, they both stared at each other – Dean confused, Lee looking almost…scared? But before Dean could say anything, Lee had grabbed his stuff and run off. 

Dean shrugged it off, figuring that Lee just wasn’t quite as heteroflexible as he had been recently discovering he was; no big deal. And at school, Lee acted like nothing had happened, so Dean just followed his lead. Then Lee led him behind the bleachers after classes. Dean turned, expecting some sort of heart-to-heart or no-homo talk, but instead Lee just started kissing him again. 

It became a pattern, Lee dragging him into corners and kissing him senseless, but neither boy ever really talked about it. It just kept happening.

One particularly hot makeout in the garage got interrupted by Sammy, and Lee couldn’t get out of there fast enough. Faced with Sammy’s probing questions, Dean caved. Yes, he and Lee had been making out a lot; no, he didn’t know why; no, he and Lee hadn’t talked about it – like, at all; and no, no one else knew. (Not knowing that Bobby had already come across them a few days previous and decided to not say anything.)

Sam was worried, to say the least. “Dean, do you really think that being someone’s dirty secret is – well, okay?”

Dean just shrugged. “He makes me forget, Sammy – forget about Dad and the future and – everything. Just – can you leave it alone? Please?”

So Sammy promised not to say anything, which was all Dean would say when Lee grilled him. Sammy would keep quiet, he wasn’t going to say anything, he would never, there was nothing to worry about. Lee still eyed Sam distrustfully and didn’t say much around him, but he never challenged Dean’s claims either, never confronted Sam, so Dean just ignored the rest of it. 

Seeing Lee’s reaction only worried Sam more, but he knew that Dean wouldn’t listen, and – well. He didn’t want to out Dean to Bobby or his mom, so he just resolved to keep a close eye on both Lee and Dean. 

*~*

As he started exploring his heteroflexibility with Lee, Dean started thinking about something he hadn’t thought about in a long time – his life-changing encounter with a certain Rhonda Hurley…and her underwear. 

As Valentine’s Day rolled closer, Dean was struck with a brilliant idea. He had a bunch of extra cash from working in the garage; why not buy himself a little treat? Despite his nerves, he visited the local mall with a mission in mind – a visit to Victoria’s Secret. 

He was fingering a pair of pink, silk panties when a saleswoman walked up to him. “Getting a pair for your girlfriend?” she asked, smiling kindly at the heated flush that immediately spread over Dean’s face. But he nodded. “Great! Do you know her size?”

“I – uh – no, not really,” Dean stuttered. 

“No worries! If you can give a guess – I’d aim a little high just to be safe – she can always return them later, she’ll have thirty days!”

“That’s – yeah, that’s good to know, thanks,” Dean replied, blush somehow intensifying. He knew he would never again walk into this store, especially not to return underwear that was supposedly for his girlfriend. So he just grabbed the second-largest size they had in the pink silk, figuring that was probably close enough, and checked out as fast as possible before booking it out of the mall. 

He hid the trademark pink bag in a much larger shopping bag he had purposely brought with him for camouflage purposes and rushed upstairs when he got home. 

He couldn’t help himself; he had to try them on. Now. So that’s what he did, stripping down and slipping on the smooth underwear. He had guessed right, the panties fit him like a glove, cupping his ass and rubbing his dick in a really…new way. He angled himself in the mirror, looking at himself and just…enjoying the feeling. 

Dean was so distracted he didn’t hear Sam’s yell up the stairs that Lee had arrived, Lee’s clomping run, or the perfunctory knock that heralded Lee’s entrance – but he sure heard the door open, just in time to whirl around and face Lee head-on. Definitely no time to hide what he was wearing – or, more to the point, what he wasn’t wearing. 

He and Lee hadn’t really gotten to the below-the-clothes action point yet, so now Dean wasn’t only wearing panties in front of his makeout buddy…he wasn’t wearing any real clothes either, for the first time. 

He shouldn’t have been worried.

Lee was immediately all over him, right up against Dean’s back, turning him so they both faced the mirror. “Is this what you like, sweetheart?” he purred. “Wearing panties, feeling like a pretty little girl?” 

Dean’s breath caught at that, and his dick started getting interested in the proceedings.

“Ohh, you do,” Lee smirked, sliding his hands down Dean’s sides to grab his ass and rub up against it. He only did it twice before Dean found himself coming hard, ruining the expensive underwear – but he had to admit, that orgasm was almost worth it. Too bad he only had the one pair.

*~*

Lee definitely liked the panties. After Dean mentioned he had only bought the one pair and didn’t have any more, Lee – got more. Somehow. 

Suddenly Lee didn’t want to do anything until he saw that Dean was wearing something Lee had brought him underneath his normal pair of jeans. Then Lee would be all hands, rubbing all over Dean’s ass, crooning all sorts of nicknames; baby girl, babydoll, sweetheart. But it was “good girl” that was Dean’s favorite and got the loudest moans; Lee used it sparingly.

And when Lee accidentally found out that Dean’s nipples were sensitive – well. Nothing would do after that but Dean crawling into Lee’s lap, Dean’s back to Lee’s chest, so that Lee could rub up against Dean’s panties, whisper all sorts of nicknames and praise into his ear, and play with his nipples all at the same time. 

Dean…well, maybe it made him less of a man in men like his father’s eyes, but he enjoyed every minute. He had no idea he was so damn kinky before this, but it blanked out his mind like nothing else, so he just enjoyed the ride.

He didn’t love Lee’s habit of getting him off and almost immediately disentangling himself, giving Dean a quick kiss and disappearing, but – Dean could handle it. 

Sammy always appeared soon afterward and wanted help with his homework, got all up in Dean’s space while asking his questions. Even though Dean would have usually grumbled about chick flick moments, after Lee’s brusque exits…it felt nice to be needed, to be cuddled a little, so he never said a word.

(He never figured out that Sam hovered by the door any time Lee came in with Dean, watching to see when Lee left so he could go give his brother the aftercare Lee was neglecting. Just because he was asexual didn’t mean he couldn’t look things up on the Internet. After the first few times Sam clocked Dean as being especially grumpy after Lee left – and knowing at least a little bit of what they were up to, because Dean was not very good at hiding all the new…additions to his wardrobe, which Sam wished he never had to know about – he looked up Dean’s symptoms and stumbled onto a BDSM webpage on aftercare. Sam knew that Dean would never talk to Lee about what he needed – too much the macho man, still – so Sam just quietly took the task on himself.)

*~*

And as the year wore on, Dean and Lee’s friends got more and more curious about the girls that were clearly keeping the two so busy outside of school. Really, the group was more interested in Lee’s mystery girl – Dean claimed that his missing time went to work…which wasn’t exactly a lie. Lee, on the other hand, couldn’t come up with an excuse but also refused to say anything about the girl, so the group just got more and more curious.

Finally, on the last day of school, one of the guys got Lee in a headlock and wouldn’t let him out until he told them *something.* 

“Oh my god, y’all’re way too invested in my love life,” Lee groaned.

“Yeah, yeah, just tell us!” the boys crowed, eager for the details as Dean just rolled his eyes behind them all, not convinced Lee was actually going to spill.

So of course, Lee smirked as he made eye contact with Dean. “Her name’s Dee, or at least that’s what she told me to call her,” Lee started to drawl. “She’s got gorgeous green eyes, greener than I’ve ever seen – and the softest lips, blows my mind every time I get to kiss them. And don’t get me started on that ass, finer than a Georgia peach and twice as sweet – ” 

“Really?” Dean couldn’t help groaning in exasperation, hoping no one else noticed the blush he could feel starting on his face. “You gotta tell us all that? And here I thought you were a gentleman who didn’t kiss and tell!”

Lee grinned and licked his lips. “What can I say? I’m a lucky man, and it’s time everyone knew it,” he leered.

And that? That was a low blow. Dean glared. “Glad you got that off your chest, then,” he snarled before spinning around and walking off, ignoring the calls behind him. 

He had made it most of the way down the hall when Lee caught up with him. “Dean, I – I’m sorry, I – I got carried away – ” Lee started before Dean held up a hand. 

“I don’t want to hear it, Lee, that was below the belt and you know it. *You’re* the one who wanted to keep this quiet, not me!”

“I know, I know, and – ”

“And nothing! Make up your mind!” Dean growled before continuing to stalk down the hall.

Lee walked quietly behind him until they were coming up on the boy’s bathrooms; then he made his move, quickly grabbing Dean’s arm and dragging him inside.

“No, Lee, I don’t – ” Dean started to protest – before freezing as Lee cozied up behind him.

“You a hundred percent sure about that, babydoll?” Lee rumbled in his ear as he roughly cupped Dean’s dick. “Cuz it sure feels like your bottom half has another opinion.”

Dean gasped at the friction, starting to grind into it as Lee slowly increased the pressure. While one hand was in front, the other was slowly working its way under Dean’s pants – and found smooth silk instead of the expected cotton.

At that, Lee let out a moan of his own and stopped Dean’s grinding to yank Dean’s jeans down and spin Dean to face him. “Did my good girl secretly wear her panties all day long at school?” Lee panted out, attacking Dean’s mouth before he could answer. 

He kissed Dean until both their heads were spinning, and their kiss was more like breathing each other’s air. 

“Looks like you are my good girl,” Lee purred after he caught his breath, “and good girls get rewards.” He spun Dean around again and got his hands underneath Dean’s shirt, pinching and playing with Dean’s nipples until Dean couldn’t take anymore and came, ruining his underwear. 

“Oh no, baby girl, did you make a mess in your panties?” Lee smirked and reached into the biggest pocket of his cargoes. “Luckily for you, I came prepared,” he continued as he pulled out another pair of panties, black silk ones in a little baggie.

“Why don’t you go ahead and switch those out, put the old ones in the bag for me, okay sweetheart?”

Dazed from his orgasm, Dean obeyed, only going into a stall for privacy once Lee shooed him towards it. Almost robotically, he pulled off the dirty pair, wiped himself down, put the dirty ones away, slid on his clean new ones and then his jeans. 

“Look at you, such a good girl,” Lee crooned as Dean stumbled back towards him. He plucked the bag from Dean’s listless fingers and stuffed it back in his cargo pocket before snaking an arm around Dean’s waist. “Keeping ‘em for later,” he winked before planting one last bruising kiss. “Bye, Dean,” he waved as he walked out, Dean left a blushing mess. 

He stood there, mind in a haze, for way too long until his phone buzzed. Sammy was wondering where he was, why Dean wasn’t waiting for him at the Impala. Dean immediately headed towards the parking lot, not knowing yet that this is the last time he would ever see or even talk to Lee – the bastard shipped out for military training the very next day.

When Dean still hadn’t heard from Lee three days later, he called one of Lee’s hockey buddies. He told Dean that Lee had volunteered for the army months ago and told everyone else that he didn’t plan to keep in contact, was going to change his phone number. Everyone knew, aside from Dean.

And it shattered what was left of his heart.


	4. Sam I

Sam stood at the window and watched Cas and Dean drive off, brow furrowed as he worried. Dean had been pretty affected by Lee’s disappearing act after their…relationship, to the point that he had barely even mentioned the name again. Sam wasn’t sure why Bobby had decided to say something, but…Sam was going to have to try and keep an eye on Dean over the next couple weeks. Cas would probably help him, and maybe he could make a quick trip out to the school by the end of the month…

Sam’s musing was interrupted by Bobby coming up behind him. “Is there anything I should know about Dean’s senior year?” Bobby rumbled. “Dean…wasn’t forthcoming.”

Sam couldn’t help letting out a bitter laugh at the understatement. “I don’t know the full story,” he warned as he turned to face the man who was, for all intents and purposes, his father. John be damned.

Bobby just settled pointedly into his recliner.

Sam sighed. “I guess you know that Dean and Lee were…more than friends?”

Bobby snorted. “No one kisses their friends like that.”

Sam chuckled. “No, I guess not.” He sighed. “Did you ever figure out when it ended? Or why?”

Bobby looked up at the ceiling as he thought. “When was early summer after senior year, boy was mopey enough, but as to why or how…I got no clue.”

Sam nodded. “Yeah, that’s about when it happened. But before I get there – did you know that Dean was Lee’s dirty little secret? I was – or, well, we thought I was the only one who knew.”

Bobby scowled. “No, no I did not.”

“Probably should have guessed that. Well, I did know, Dean made it pretty clear, but – he also said that their – their thing was helping him get over Dad, so. He asked me not to interfere, and like an idiot, I promised him I wouldn’t. They got…more intense – ” 

“How intense?” Bobby interrupted.

Sam groaned. “Please don’t make me describe Dean’s sex life. You really don’t want to know, and I wish I hadn’t found out. They weren’t doing anything unsafe, just…intense.”

Bobby chewed on that for a minute or two before waving for Sam to continue.

Sam blew out a breath. “Thank you. So, it had gotten intense. Maybe more intense than Lee expected? Whatever the case, something happened on the last day of classes – Dean never told me exactly what, which is probably good for my sanity – and, in his own way, Lee must have been saying goodbye. Because, as it turns out, Lee had gotten on a plane bound for an army base the very next day. With a new phone in his pocket. Apparently he had warned everyone besides Dean that he planned to basically cut contact with everyone once he left. Dean didn’t even know that he had planned to join the military, and especially with Dad so recent…” 

Sam fell silent before continuing. “Well, it really screwed Dean up. Lee broke his heart, and reopened Dean’s wounds. So yeah, Dean moped. Understandably so. But it was more than that – Dean started worrying again. About the future Dad wanted for him, and whether that was better than staying close to home and working with cars. All on top of figuring out that he wasn’t quite as straight as he had kinda always thought, and what that meant for him after growing up with Dad for so long.” Sam shrugged. “Or, at least, that’s what I think was going on. You know how Dean can be.”

Bobby nodded.

“I helped him figure out more about his labels, at least, so that was one less thing for him to worry about; but he wouldn’t listen to me when it came to the Naval Academy. Kept insisting that if it’s what Dad wanted, it had to be important. Never mind that Dad never prioritized our wants and dreams above his own,” Sam snorted. “I still think that a lot of that was the grief talking – Lee was a distraction from the grieving process, him leaving just started it all over again and left Dean wanting to fulfill Dad’s last wish, as shitty as it was.”

Bobby nodded. “Your brother always was a little quick to the self-sacrificial altar,” he responded slowly. 

Sam smirked. “You can say that again. But yeah, that’s basically what happened, and then…you talked him out of making what could have been the biggest mistake of his life. But talking about Lee today…I don’t think that Dean’s going to end up handling it well.”

Bobby grunted. “Depends how well Cas handles it.”

Sam turned to look at Bobby. “What has Cas got to do with it?”

Bobby just chuckled. “Maybe you’re just too young to see it, kid,” he started, ruffling Sam’s mop of hair, “but Dean is looking at Cas almost exactly the way he looked at Lee. If your brother isn’t nursing some sort of feelings for Cas, I’ll eat my hat.”

Sam wrinkled his nose. “But Cas is my friend,” he whined. “Can’t Dean just…like someone else?”

“The heart wants what it wants, kid, it’s not like we get a lot of choice in the matter,” Bobby laughed. “But I will say…doesn’t look like Dean knows he likes Cas, and even once he figures it out…he seemed pretty skittish at the idea of Cas and feelings when I was talking to him earlier. You think this thing with Lee – ?”

Sam groaned. “Of course, Cas is the first guy Dean’s had a crush on since his thing with Lee crashed and burned. Crap. Dean is not going to deal with this well,” he muttered as he turned back to look outside. “I have got to visit Dean sooner rather than later.”

Bobby sighed. “That would probably be wise. But for now, we might as well get dinner started.”


	5. Cas II

The drive back to campus was entirely silent. Cas focused on driving and only glanced at Dean’s closed eyes and tense body language every now and then; he was afraid of what might happen if he tried to turn on any music. Instead he drove to the soundtrack of his own worried thoughts about the boy next to him, and whatever the person named Lee had done to him that the mere mention of the name had Dean so tense. Hopefully he could get answers sooner rather than later.

*~*

Once they reached campus, Dean tersely instructed Cas where to park and walked him to his dorm, still silent otherwise. He only waved to Cas’ tentative “Good night,” but Cas had expected that – and the couple days of silence that followed. What he had *not* expected was the seven (and counting) days of silence, especially when Sam’s texts about Dean grew increasingly worried as Cas continued to have nothing to tell him. Sam wanted to visit, badly, but some big school project had come up and he didn’t have the time – which only left him more frustrated at his own powerlessness. Cas was on campus, but…every time he tried to talk to Dean, the older Winchester brother would wiggle out of it; he would find any excuse to be anywhere else. 

Finally, after day fourteen of this nonsense, Cas’ patience snapped. It was time to bring out the big guns. So he once again tried to sit down with Dean at his usual lunch table, and (as usual) Dean left almost as soon as Cas sat down. But this time, instead of leaving soon afterwards, Cas stayed. “I…apologize for the intrusion, but…I’m getting desperate,” he started, looking at each of Dean’s friends. “I have been trying to talk to Dean at the behest of his brother Sam for two weeks now, with no luck. Do you, perhaps, have any advice?”

The girl with wavy red hair seemed the most receptive to his request, brow furrowing in thought at the mention of Sam. “Dean has been pretty out of sorts lately, even for him…” she murmured. Mostly to herself, although Cas was close enough to hear it. He held his breath – maybe this friend was the answer to his problems?

She finally turned to face him head on, a determined look on her face. “Yeah, okay. I can help you. Come on, you and I need to talk over our options.” She stood and waited for Cas to follow her. As they were walking, she suddenly turned and stuck out her hand. “Sorry, I forgot – I’m Charlie.”

“Castiel,” Cas replied as he shook her hand. “But Dean and Sam call me Cas, and you are welcome to do the same if you prefer.”

She grinned at him. “Thanks, Cas! Now, here’s what I’m thinking…”

*~*

So, as per Charlie’s instructions, Cas showed up on Saturday night at the indicated time and indicated room. He knocked on the door and was quickly admitted. “Ah, Cas, just in time!” Charlie called from the front of the room as Dean whipped around, eyes wide. “Come on over. Guys, this is Cas, he’s serving as handmaiden tonight!”

Cas pointedly ignored Dean’s gaping, instead turning to Charlie and raising an eyebrow. “…Is there a reason for the title?”

Charlie smirked. “Yep, someone whose name begins with a D and ends with an -ean. He kept grumbling that having to just sit and watch wasn’t all that much fun, so I gave him a title and a couple responsibilities to fulfill. Speaking of! Did you remember them?”

“Of course,” Cas rummaged around in the bag he had brought. “Chocolate-covered espresso beans for her highness – ” Charlie took the box with a happy squeal. “ – and a number of different snacking options for the rest of the group. White cheddar popcorn, tortilla chips, pretzels, Double-Stuf Oreos – which I am told are the superior choice – and...” He hesitated before pulling out the last few items, which Sam had sworn were the right choice but he was still worried about. “...assorted flavors of beef jerky?”

To Sam’s credit, Dean immediately perked up. “Alright, you even got my favorite brand!” he cheered. “Charlie always forgets and asks for the wrong kind.”

Cas smiled. “I did have help, to be fair.”

“Sammy’s the best.”

Charlie clapped her hands sharply. “Okay, people, enough chit-chat! It’s time we get back to where we last left our intrepid heroes – does everyone have their character sheets ready? Yes, good, then – we last left our intrepid heroes having defeated a horde of kobolds on their way towards their true goal…” 

Cas zoned out a little, missing the rest of Charlie’s speech as his father’s past ranting on the evils of the Satan-worshipping game rang in his ears. He pushed it away, not wanting to judge his new friends based on their interest in something that neither his father nor he had ever even experienced; and here was his chance. 

And what he found was…nothing at all what he expected. Dungeons & Dragons was a strategic war game – not all that different from RISK, one of his father’s favorite games. Battles were similarly dependent on dice, and players’ excited or disappointed cries were familiar. The main difference, as far as Cas could tell, was the unpredictability of the plot, as it was character-driven, so even straightforward goals could be sidetracked by unexpected obstacles or character thought processes. 

But even so, there was a goal to be achieved, and while violence was often used to achieve progress towards that goal – well, there was in RISK as well. Supernatural and roleplaying elements aside, there wasn’t enough difference in the two games to justify his father’s deep-seated hatred for one and love of the other – D&D was nowhere near the “devil worship” that his father ranted about. 

In any case, shifting worldview or not, Cas truly enjoyed getting to watch Dean and his friends play this fascinating game, reveling in their victories and bemoaning their defeats; unable to fully follow the plot of their adventure, as he was entering mid-campaign, but he was quickly sucked into the chaotic energy nonetheless, and when the session began to wrap up, Cas was shocked to see that it had been over four hours since he had walked in the door – and even more shocked to find that he was disappointed that it was over.

Perhaps…perhaps this was something Cas would want to try, when they started their next – what had Charlie called it? Ah yes, their next campaign. 

Speaking of – Charlie grinned over at him as she started to pack up her materials. “Pretty amazing, isn’t it?”

Cas beamed back at her. “It was fantastic! And here, let me help – ” 

And as he got up to help Charlie wrangle all her dice and set-up, Charlie frowned. “Hard to do it by yourself – DEAN! Dean, why don’t you come over here and help Cas, make sure he doesn’t pack anything wrong, ‘kay?”

Dean froze by the door, clearly weighing his options; Charlie’s pointedly cleared throat tipped the scales and he trudged back to where Cas was carefully starting to gather the indicated items. Quickly and efficiently, Dean instructed Cas as to how Charlie liked everything packed away – for ease of unpacking next time, apparently – and they got the task done. 

Bidding Cas a quick goodnight, Dean made a break for the door again – only for Charlie to suddenly loom in his face, bright grin in place. “You have a choice, Dean Winchester. You sit down and talk to Cas tonight – or at the very least, make plans to talk at a better time, it is pretty late – or I swear to the geek gods, you stubborn bastard, I *will* lock you two in a closet. Capiche?”

Dean’s jaw dropped. “I – ”

Charlie put up a hand, three fingers raised. “Talk now, talk later, or closet?”

Dean snarled wordlessly before spitting out, “Later.”

“Cool, when’s good for you, Cas?”

Cas jumped at his abrupt inclusion in the conversation. “Uh, lunch tomorrow would be fine, if that works for your schedule, Dean?”

Charlie raised an eyebrow at Dean. “I – yeah, yeah that’s fine,” Dean grumbled. 

“Great! See you two later. And don’t forget to let Sam know about this, Cas, he’ll help hold Dean accountable,” Charlie chirped as she left. 

The second she did, Dean whirled to glare at Cas. “Getting Charlie involved is dirty pool, Cas!”

Cas just sighed. “How much longer were you going to ignore me without her intervention?”

Dean looked away. 

“Exactly. Dirty pool or not, it’s time. Sam has been trying to get you to talk to either me or him since we left, but he can’t do much to convince you from where he is. And you do need to talk, Dean, no matter what you think – Sam believes that it’s been eating you up inside, and Charlie has definitely noticed something is going on. Just…please? I just want to help you, Dean.”

Dean was silent for a few minutes – minutes in which Cas could hear nothing but the ticking of the clock and his pulse pounding in his ears – but then Dean sighed. “Fine. FINE. Lunch, tomorrow. We’ll get food in the cafeteria, then head to an empty classroom to…talk, alright?”

Cas’ responding smile felt like it should have lit up the room. “Yes! Thank you, Dean. I’ll see you tomorrow.”

Cas went home satisfied with the day’s productivity: he had finally gotten Dean to agree to talk to him, thanks to Charlie, and he had also discovered an exciting possible new hobby. He would have to participate in a future campaign to know for sure, of course, but he had a good feeling. He was…worried about what Dean might reveal during their talk tomorrow, but it was important for Dean to talk about whatever had happened. 

Cas hoped that Dean talking to him would be as effective as Sam seemed to think it would be.

*~*

The next day, Cas found himself more distracted than usual during his classes – still taking his impeccable notes as usual, that was a habit too well-ingrained to ignore, but there was also a small corner of his brain doing nothing other than counting the minutes until his lunch break. When the last bell finally rang, Cas packed up and practically sprinted for the cafeteria; the faster he could his food and be ready to leave with Dean, the less the other boy had to change his mind. And Cas, Sam and Charlie would all be so disappointed if Dean backed out and wasted all their hard work. 

So when Cas’ mad dash paid off, leaving him ready and waiting as Dean retrieved his own meal, he was relieved. He was going to help his friend, no matter what it took; whatever Dean had to say, Cas was ready to listen.


	6. Dean II

**Summary for the Chapter:**

> Recap of the flashback chapter within! A much milder telling, but just in case, those warnings still apply.

After his trip down memory lane, Dean was…out of sorts. He knew, if Cas asked the wrong question or said the wrong thing, Dean would bite his head off. But Cas was a friend – maybe, possibly, more than that, but Dean wasn’t willing to go there yet, nope-nope-nope – and didn’t deserve being the target of Dean’s building ire. So Dean was as silent as possible, willing himself to contain, contain, contain until he had a safe target – most likely his favorite punching bag at the gym. 

But even though his workout helped, he still knew that he was nowhere near ready to talk to Cas about…any of it. Not Lee, not why he was still so upset; for once, he just had no idea what he could possibly talk to Cas about. So he didn’t. He canceled their next pop culture night and ignored all of Cas’ attempts to reschedule until Cas stopped asking about them, but he never gave up on trying to talk to Dean at lunch, no matter how many times Dean pushed him away. It got to the point that Dean realized he was being a total asshole, shutting Cas out like this…which only caused him to push Cas away harder, because Cas didn’t deserve any of Dean’s bullshit in his life. 

…If only doing what was best for Cas didn’t hurt so much. 

(Somewhere, deep down, Dean knew that if Sam had any idea what Dean was thinking, what Dean was doing, Sam would smack him and/or talk some sense into him, but…Sam wasn’t here. Dean was just going to keep digging himself deeper and deeper. This was a bed of his own making and he was just going to have to lie in it.)

*~*

And then, it was time for Charlie’s bi-weekly D&D session – and Dean was so very ready to be someone else, even if it was only for a few hours. He was going to get to escape thoughts about Cas, if only for a little while.

…So of course, right as he got settled and ready to play, who else but Cas walked in. Dean was all ready to get up and go, claim a sudden onset sickness, but Cas…Cas had bought his favorite jerky. Not just his favorite brand, but a number of his favorite flavors. 

Dean could not, okay? The best way to his heart was through his stomach and his brother, and unfortunately (fortunately?), Cas had already mastered the latter and was well on his way to mastering the former. Dean knew he was in trouble, but this? This just sealed the deal – maybe Cas didn’t deserve Dean’s bullshit, but Dean didn’t care anymore; this was not someone he could allow to get away without a fight.

…He was going to tell Cas. After he got through their marathon D&D session and got some sleep, the first thing he was going to do was talk to Cas. 

*~*

By the time they wrapped up, even with all Cas’ jerky to keep up his energy during the session, Dean was *exhausted.* He just wanted to get some sleep, then talk to Cas until his face turned blue, once he had full control of his brain and tongue again.

Instead, Charlie, the worst friend in the world, decided to stick her nose into it, and Dean, instead of explaining that he already had a plan, thank you very much, followed her lead. Then, Cas – Cas asked him to talk about the one thing he didn’t think he physically could, but…this was Cas. Cas, who made friends with his geek brother, who made sure to bring his favorite food to D&D, who always asked the strangest questions about pop culture, and who, apparently, just wanted to help Dean. And so Dean folded like a cheap suit and succumbed to Charlie’s threats, Sam’s requests, and Cas’ pleas; he was going to talk to Cas. About it all. Maybe it actually would help. 

…Or maybe he would regret it later.

But at least he would have tried.

*~*

As the time to talk grew closer and closer, Dean couldn’t pay attention in class. (He would have to get the notes later.)

No, all he could focus on was talking himself out of talking himself out of talking to Cas. 

He had to admit, his previous solution of just – not thinking about Lee only worked until the name came up again; now that Lee was back in his thoughts, haunting him again, he…couldn’t forget. And he had no other defenses. Maybe Sammy was right, maybe talking about it, purging some of his feelings would help.

…Especially knowing that Cas…didn’t have context. Cas had never met Lee, never met his father, hadn’t had the chance to form…opinions the way Sammy had. No prejudice or preconceived notions clouding his judgment, just Dean telling his side of the story to a blank slate.

…That. That actually sounded pretty great, now that Dean was thinking about it. Not that this was a topic he would ever enjoy discussing, but at least…at least he got that much. He could work with that.

*~*

Dean couldn’t help smiling at Cas’ eager beaver status when he reached the cafeteria, even as his stomach twisted at the thought of eating; but still, he gathered some soup, crackers and bread, figuring a lighter meal would be easier to force down during this conversation.

When they sat down in the empty classroom they had found, Dean made sure to sit next to rather than in front of Cas; he wasn’t sure if he could say what needed to be said while looking Cas in the face. 

Once they were settled, Cas starting to eat and Dean starting to pick at least a little at his food, Dean began to speak.

*~*

“I think…to explain Lee, you have to know – the summer before I met him, my father died. And…not that my dad didn’t have his issues, because he did, there’s a reason Mom divorced the bastard – but. Sammy had just come out to me as ace, and all I could think was how much easier he would have it if Dad never came home. And then, of course, he didn’t.” 

Dean took a deep breath.

“So, yeah, a lot of guilt mixed in with grieving, and then…Lee came along. And we were friends, it was good, but then – we kissed. And Lee ran away, so I figured that was the end of it, but…then it wasn’t. Next thing I know, Lee and I are – secret makeout buddies? I don’t know what we were, exactly, we weren’t exactly talking with each other’s tongues in the way,” Dean snorted. 

“Sammy was pretty upset when he found out, mostly worried that Lee wasn’t treating me right – which, in retrospect, of course, Sammy was totally right, but, right then…Lee made me forget,” Dean confessed quietly. “He made me forget about my guilt, about my grief, about – about the future. He grounded me in the moment, that was all I could think about when I was with him, and it felt so good. I mean, looking back, Lee was more like an addiction than anything healthy, but…at the time, it felt like he was all that was keeping me together, and if Sammy had ruined that…well. I don’t want to even think about what could have happened, but luckily Sammy backed off and just…let me enjoy my horrible coping mechanism in peace,” Dean chuckled bitterly.

“And, I mean, part of it was – I was only just realizing I wasn’t completely straight, right? It was a pretty recent development before the kiss, and then…then things with Lee got a lot more hot and heavy. I mean, no penetration or anything,” Dean continued quickly, “but…there were definitely orgasms.” He paused. “Almost all of them mine, actually, now that I’m thinking about it,” he continued distantly before shaking his head. “Suffice to say, things got…a lot more intense. And I missed a lot of warning signs. The last day of school…” 

Dean cleared his throat, busying himself with his food for a few moments. “The last day of school, we…had one last encounter. And then, then Lee flew off to his military training – the military training he had neglected to mention to me at all, after knowing, *knowing* that’s how my dad died, and – ” Dean took a deep breath. “Yeah. Changed his phone number, too, had to figure out why my calls and texts stopped going through after talking to a mutual friend. And everyone knew what he was going to do – everyone except me and Sammy, and, well…like all those stupid songs, Lee broke my heart into a million pieces. And Sammy’s probably right, I probably had been using Lee as a bit of a – well, a crutch, to avoid dealing with my grief, and with Lee leaving like he did, on top of everything else…” 

Dean went silent. “Let’s just say it was bad,” he finally continued. “And Lee being my first…anything since figuring out I…wasn’t straight, there was some…”

He hesitated, fists clenching and unclenching. How could he put this, without sounding like the wimp he still kinda felt it made him, no matter how many times Sam told him the opposite?

But the words didn’t come to him, and finally Cas interjected quietly. “Lee was your first boyfriend – or, at least, non-girlfriend – and him leaving you behind like that…it must have hurt quite a lot.”

Dean shook his head, teeth gritted. “No. Or, well, yes, but – it was more than that. I – Lee was military, Dad was military. I never felt like I was good enough for Dad, and then – then I wasn’t good enough for Lee. They were both homophobic dickwads, in their own ways, and – ” Dean waved a hand helplessly.

Cas spoke up softly again. “…And rejection from both of them started to feel like a pattern?”

Dean suddenly turned to face him, mouth open in shock. “Yeah,” he whispered. “Yeah, that – that sounds about right.” He cleared his throat and faced forward again. “So, Sammy and I started talking, a lot. He was helping me figure stuff out – I mean, I knew I wasn’t straight, but I didn’t really know any more than that. It took a little while, but we figured out I was bi and – maybe demiromantic? Not as sure about that one, but yeah. Of course figuring out that being bi is just as bad as – or worse than – being straight in some circles didn’t exactly help with the rejection thing,” Dean grimaced. 

“So between that, grieving Dad and recovering from Lee’s bullshit, I…I took a gap year. Worked at Bobby’s garage, tried to figure out what my future should look like…and finally decided I liked working with cars enough to make it a career, and I knew I wanted to stay close to home, so – here I am. Still healing, I guess, if Bobby mentioning Lee was able to make me tailspin like that.”

Dean finally lapsed into silence, feeling…well, kinda relieved to get it all out? But also just…hollowed out. He focused on munching on his stale crackers and bread, ignoring the long-cold soup.

Cas eventually cleared his throat. “Dean, may I ask you something?”

“Sure, Cas.”

“…May I hug you?”

Dean turned to face him. “I – sure?”

Cas clambered out of his desk, and gestured for Dean to do the same. After Dean had obeyed, the slighter shorter man held out his arms in invitation, and Dean – Dean was going to just give Cas a brief hug, but…he hadn’t realized how bad he needed one until he started practically melting into Cas’ embrace. Cas made soothing noises as Dean tightened his grip and buried his head into Cas’ shoulder. This…this was nice. Dean definitely wanted to do this again, as many times as Cas would let him.

…And with that, Dean started to really, truly fall in love with Castiel Adler.

*~*

Which, Dean quickly realized, was a bad idea. The last time he tried starting anything with a friend was – well, Lee. And look how that had turned out. 

Not that he thought Cas would be anything like Lee, but…hindsight was 20/20. He never would have thought Lee would do anything like that, either, when they were just friends. Not to mention that Cas was ace, anyway – he vaguely remembered Sammy saying something about ace people not dating. So Dean just needed to ignore these stupid feelings; they would go away eventually. For now, he had movie nights to plan.

*~*

And of course, just as Dean was wrapping up his plans for the month, Sammy called.

“Yeah, Sammy?” Dean asked distractedly as he pulled up the next month on his calendar. He had shown Cas a couple Pixar movies by then, but it was probably time to at least think about adding in some Disney movies too…

“Dean, stop whatever else you’re doing. This is important.”

Dean immediately snapped to attention. “Sammy, are you okay?”

Sammy groaned. “Yes, I promise I’m not in any physical distress.”

Dean smirked. If he wasn’t in any kind of physical trouble, but he still wanted Dean’s help… “What’s her name?”

“I – wh – how did you know??” Sammy sputtered into the phone. “For all you know, she could be a he!”

“Yeah, okay, spare me the pathetic attempts at distraction,” Dean drawled. “What’s her name?”

“…Sarah,” Sammy finally muttered. “She’s in my art history class.”

Dean cackled. “Smart and pretty – nice Sammy!”

“Shut up, jerk! This is not why I called,” Sammy growled back.

Dean frowned. “Why did you call? I thought ace people weren’t interested in dating.”

Sammy’s sigh into the phone was long and exasperated. “Seriously? Do you listen to a single word I say?”

“…No seriously, I definitely remember you saying something along those lines.”

Sam groaned. “Dean. I said that most *aromantic* people have no interest in dating; while there are a number of aromantic asexual people, there are also plenty of alloromantic asexual people – like me, meaning that even if we’re not sexually attracted to people, we are romantically attracted and interested in the whole dating thing. Even if most of us don’t have a ton of practice…hence this call,” Sammy grumbled. 

Dean smirked. “Aw, Sammy’s asking for tips on getting his first date!”

“I – ” Sammy groaned again. “I wish I could disagree with that, but it’s true. Now do you have any tips or not?”

Dean gave advice mostly on autopilot, vaguely registering Sammy’s happy tone at the conclusion of their conversation and that he must have done a good job; but most of his brain was processing that ace people did date. Maybe…maybe he and Cas weren’t quite as bad of an idea as he had originally thought? 

That little epiphany lasted for all of five minutes after Sam had hung up before Dean remembered what Cas had said at their first real meeting, when Dean had asked for his phone number – Cas wasn’t interested in dating. 

Dean shook his head, frustrated with his stupidly optimistic heart. He was lucky enough to be Cas’ friend; it was time to bury his feelings as deep as he could and just be happy with what he had.


	7. Cas III

Castiel wasn’t sure what he had been expecting Dean to tell him about Lee, but – it wasn’t all of that. His dad dying, Lee compounding that grief with his…*despicable* treatment of Dean and abrupt exit, then Dean figuring out that his identity was still not enough to ensure acceptance from the community or society at large – that it could put a target on his back…

And despite all of that, Dean was…not only still standing, but – well, thriving. Part of a large social circle, pursuing his dreams, doing well in school, taking care of his brother…taking Cas under his wing, too. How did such a good and kind person go through so much and…still, despite it all, take care of so many others? 

Cas wasn’t sure how he could help Dean, not really, but…a hug couldn’t hurt. And the way Dean melted into it…it did seem to really help. Cas started to wonder if Dean was touch-starved, and resolved to try and alleviate it going forward. It was the least he could do.

*~*

At first, Dean seemed surprised by Cas’ sudden touchiness – which, to be fair, Cas was not usually one to initiate physical contact, since so many took it to mean something far different than he intended. But…this was Dean. Dean wasn’t interested in Cas, he wouldn’t take it the wrong way, so Cas was happy to open his personal boundaries to include one Dean Winchester. 

(And if he was also mitigating his own slight touch-starvation…well, no one needed to know that.)

While he gave Cas some looks at first, Dean soon adjusted to the new normal and started initiating his own platonic touches, to the point that even in public, the two were almost constantly touching.

…And even if the boys didn’t notice how quickly they had become so comfortable with each other, their friends certainly did.

“Sooo, when did you two start dating?” Meg asked slyly one day at lunch. 

Cas flinched and Dean turned to glare at her. “We didn’t! Cas isn’t interested in dating anyway, and I wouldn’t pressure him like that,” Dean huffed.

Cas frowned. “When did I tell you that?”

Dean raised an eyebrow. “Remember when we were talking outside the library?”

Cas rolled his eyes. “Ah, so you’re taking something I told someone I thought was stalking me as entirely truthful?”

Dean just blinked at him. “…Are you saying it wasn’t?” 

Cas cleared his throat. “As it happens, it was true at the time – but. Things can change. I wouldn’t take it as an absolute or anything.”

Dean just stared at him for a second, something…something Cas couldn’t identify appearing in his eyes before disappearing just as quickly as Dean turned to ask Charlie something about an upcoming D&D session.

Cas was quiet for the rest of lunch, trying to figure out what he had missed, because a reaction like that from Dean definitely meant he was missing something.

*~*

And after that conversation, Dean was suddenly less receptive to Cas’ touch. 

…What had Cas said? He had said something wrong, he knew he had, but the one time he asked Dean about it, Dean brushed him off and Cas…Cas was afraid to ask again and make it worse.

So he decided to enlist Sam’s help. 

He scheduled a call with Sam and explained the situation: lots of touching, the conversation about perhaps being open to dating, and Dean’s sudden reluctance to accept his touch.

“I know they’re connected, but I can’t see how and Dean refused to explain when I asked him,” Cas huffed.

Sam was silent. “Sam?” Cas finally asked.

Sam sighed. “If this is what I think it is…I can’t actually tell you, not without betraying Dean’s trust,” the younger Winchester admitted. “But I can try and talk to him, see if I can get him to talk to you?”

“Please,” Cas asked quietly. “This has been...very aggravating. I just want to know how to fix it,” he whispered.

“Don’t worry Cas, I’m on it.” Sam responded reassuringly.

*~*

Cas was not expecting Sam to call back so quickly, but he answered his phone as soon as he saw the caller ID. “Yes?”

Sam blew out a sigh. “Well, Dean’s definitely gone into martyr mode.”

“I – I’m sorry? Martyr mode?”

“Yeah, he’s being a self-sacrificing idiot, which means any brother-to-brother confidentiality goes out the window until he snaps out of it. Dean’s gotten it into his head that you’re interested in dating – other people. Not him. And so, he doesn’t want your closeness with him to scare anyone off. That’s why he started acting so weird.”

Cas was struck dumb. 

“Cas?”

“That – that is the most ridiculous thing I’ve ever heard!” he finally burst out. 

“I mean…I’m with you on that one, but once Dean gets an idea in his head…” Sam trailed off.

Cas pinched the bridge of his nose. “The dating thing was entirely hypothetical anyway,” he groaned, “this is all because of Meg and her stupid question, dammit!” He blew out a frustrated breath. “Is Dean going to pull away now, more than he already has?”

Sam made a considering noise. “It’s hard to tell. I mean, it’s a definite possibility – he almost certainly knows that we’re talking right now, and he told me some pretty damning stuff, from his perspective. On the other hand, he clearly really likes you, if you’re worthy of martyr mode, so…” Sam trailed off. “Actually. He got really agitated at the idea of you being interested in dating him. That’s – that’s the part that made him hang up on me.”

Cas’ thoughts screeched to a halt. “You…you told Dean I was interested in dating him?”

“No – no, Cas, I didn’t say it was a certainty or anything, I just brought it up as a hypothetical, and Dean just…reacted really strongly,” Sam hurried to explain. “…Almost too strongly. Like…like he was certain you didn’t want to date him. Have you two already talked about this?”

Cas shook his head before remembering that Sam couldn’t see him. “N-no, not unless you count the one mention of not being interested in dating, all the way back when he gave me your phone number – and his,” Cas mumbled. “Aside from that…I mean, clearly he likes sex, and he knows I’m asexual, so maybe that’s…?”

Sam hummed thoughtfully. “I mean, maybe? I didn’t exactly get into the nuts and bolts of asexuality with him, I’m not sure he knows about the sex favorability-indifference-repulsion scale…But. You and I can speculate all day, we’re not going to be able to figure it out until Dean weighs in. He’s not going to want to talk to me for a few days, I think my little hypothetical really aggravated him. He’s either going to avoid you like the plague or pretend like absolutely nothing’s wrong, hoping that I haven’t talked to you yet. You’re going to have to see what he does – if he’s in avoidance mode, you’re going to need Charlie’s help again. Or someone else, if you have any other mutual friends you think would help you out. You need to talk to him sooner rather than later, okay Cas? The sooner you clear this up, the sooner you guys can get back to normal. Or, at least, whatever you guys want normal to be.”

Cas took a deep breath. “You’re right. Thank you, Sam. I…I don’t know what I’d do without you.”

“Wrangling my brother is a full-time job; it’s easier the more of us wranglers there are,” Sam responded cheekily. “Good luck Cas.”

“Thank you,” Cas replied before hanging up. Despite Sam’s words, Cas was pretty sure he knew what Dean was going to do; he needed to compose a text to Charlie.

*~*

As Cas suspected, Dean was definitely avoiding him – again. Cas only let him cancel pop culture night on him once before getting Charlie involved this time. But they had to be sneakier than Cas crashing D&D again; Dean would be expecting that. 

So Charlie and Cas met up at Cas’ usual library study spot (Cas knew Dean would avoid it like the plague if he was avoiding Cas, no need to worry about their plotting being discovered) and they started brainstorming. Most of Charlie’s ideas were too outlandish, in Cas’ opinion; they mostly involved locking doors and trapping Dean. Cas did remember what Charlie had threatened at the D&D session, but he also remembered how angry Dean had been at being cornered; it didn’t seem the best tactic, even if it probably would be effective once Dean stopped being angry.

Instead, Cas finally suggested a much more subtle, if simple, plan: Charlie should invite Dean to meet her for a meal – or a study session, *something* – and once Dean had agreed, Charlie could text Cas the details and when Dean arrived, Cas would be there instead of Charlie. If they were face-to-face, Cas was certain he would be able to talk Dean into staying and talking, no locked doors necessary. Charlie finally sighed loudly and agreed. She would invite Dean to discuss his D&D character leveling up, so they would meet in the same room they had played D&D in; Charlie would text him the date and time later.

Cas was pleased she had accepted his idea so readily, and left satisfied that common sense had prevailed.

*~*

Charlie had texted him that Dean was going to show up with pizza on Friday at six. A direct interference with their usual pop culture night, Cas realized bitterly, but resolutely let go of any hard feelings; that was not the point of tonight’s meeting.

At five to six, Cas was surprised to hear two sets of footsteps approaching the room – had Charlie given him the wrong time?

But no, that was Dean with pizza boxes in the doorway and…Charlie was there too? Why – 

“I warned you, Winchester!” Charlie yelled as she pushed Dean inside the room, slammed the door and locked it. “Now start talking, I’ll be back in two hours to check on you!” Her shout was only slightly muffled through the door, but her footsteps walking away sent the message pretty clearly: they were stuck here.

Dean whipped around to face Cas, face contorted into a snarl, but Cas raised his hands in the universal gesture for peace. “I swear, I had no idea she was still stuck on doing that, I thought I had talked her out of it.”

“No one can talk Charlie out of anything, dammit,” Dean grumbled as the misdirected anger bled out of his stance. He set the pizzas down and started plates for both him and Cas. “I should’ve known better when Charlie insisted on getting a cheese pizza instead of her usual multi-topping experiment of the week,” Dean sighed. 

Cas smiled softly; Charlie may have locked them in, but at least she did so after making sure that they would both be able to eat the pizza. She and Dean both knew he hated an overload of toppings on his pizza; at most places, he preferred to stick with just cheese. 

Cas quietly took the plate Dean handed him and dug in; they had gotten George’s; hands down the best pizza in the area. That was almost entirely worth being locked in like an animal.

The silence didn’t last long after the pizza was eaten. Cas decided that the best defense was an early offense, in this case. He took a deep breath. “Are you ready to talk to me about why dating me, or me dating, is such a touchy topic?”

“…Do I really have to?” Dean whined. “Can’t we just…not talk about this?”

Cas frowned darkly at him. “Perhaps, Dean, if you hadn’t decided that I had the plague over the past week and avoided me accordingly, this conversation would not have been necessary – but now? Yes. I deserve to know, and there is no way Charlie’s letting you out without us having made some progress. So please, Dean, talk to me.”

Dean turned to stare at him. “Were you just trying to say that I avoided you like the plague?”

Cas waved a hand in irritation. “My interpretation of the saying is not what’s important here, Dean,” he growled. “You need to talk to me about this, now – or else…” Cas hesitated.

“…Or else what?” Dean asked.

Cas squared his shoulders. “Or else I’m terminating our friendship,” he finally responded firmly. “I deserve better treatment than this, Dean, and I…I can’t keep doing this,” he continued despairingly. “Either we’re friends, and we communicate and depend on each other as such, or else we’re not, and we’ll go our separate ways. But you cannot keep being my friend and also shut me out when you feel like it.” Cas turned to face Dean head-on. “Please, Dean; talk to me. Help me understand.”


	8. Dean III

It would be an understatement to say that Dean was surprised by Cas’ new hands-on policy – hands on him, to be exact. Mostly on his shoulders and back, to start, but soon Cas was touching his arms, his hands, his neck – at which point Dean had already decided fuck it and was giving as good as he got. If Cas was going to be comfortable with touching now, then Dean was going to indulge his very-well-hidden-shut-up-Sammy snuggle bunny (Sam’s words, not his, Dean preferred “octopus”) habits. There was something about getting a good hug that turned Dean into putty, and he had to admit he really enjoyed returning the favor.

So everything was fine and hunky-dory, Dean living chin-deep in denial until Meg had to open her damn mouth and make it…weird.

They were two guy friends who just…happened to enjoy each other’s…touch. Oh god that sounded dirty, but...it just felt so good – and oh no that just made it worse. 

Then Cas mentioned…dating. And if Cas was thinking about dating, something Dean hadn’t even considered somehow…Cas was going to be touching someone else. Cas was going to be touching someone else like this, not Dean, and so Dean…Dean had to start learning to live without Cas’ constant touches. 

Not only to not step on a future datemate’s toes (god Dean loved that word, he wished he got to use it more often), but…no one would want to date someone that already had another person draped all over them; Dean didn’t want his (totally, completely, successfully ignored) mushy feelings that he kept indulging with all the touching getting in the way of Cas’ happiness.

Dean would be fine, Cas would find his datemate and then they would all be happy.

…Except. Cas didn’t seem to understand why Dean was suddenly giving him all his personal space back. Which. Dean was not going to explain it, okay, it was unspoken bro code and Dean was nothing if not a great friend; it was for Cas’ own good, no matter how much Cas’ sad face started to tear at Dean’s well-constructed reasoning.

*~*

Said reasoning took a pretty deep blow after Sammy called him out of the blue. 

“Sammy? You okay?”

“Yeah, Dean, I’m fine – but. Are you?”

Dean laughed. “Sammy. I’m fine. Why would you ask that?”

Sammy hesitated before saying one of the last things Dean expected to hear. “…Cas is worried about you.”

“Cas? About me?”

“Yeah, he…he thinks he did something wrong.”

Dean just gaped. “I – he didn’t do anything wrong! I just – I thought – this was for him!”

“What was for him?”

Dean sputtered. “Wh-why am I even talking with you about this anyway?”

“Because unfortunately for you, you’re a stubborn ass who can overreact and Cas didn’t want to make whatever’s going on worse, so he came to me first for advice. Do you want to talk it out with me first, or just go straight to Cas?”

Dean grumbled for a bit before caving. “I… Cas has been all up in my personal space,” he started abruptly, “and it was really nice, actually. But then he said he was interested in dating, and if anyone he might be interested in dating sees us all over each other…it won’t end well. So, you know, I’ve stopped most of it,” Dean half-shrugged, trying to play it cool before realizing Sam couldn’t see him and abandoning the gesture. 

Sam sighed. “Okay, and you didn’t explain this to Cas, because?”

“Because! I didn’t think I had to; I thought it was obvious!”

Sam groaned. “Okay, maybe to you, but all Cas saw was you pulling away for no real reason. And…Dean, if Cas was comfortable with you being in his space, and expressed an interest in dating in front of you…how do you know the person he was interested in dating wasn’t…well, you?”

“That’s not funny, Sam,” Dean snapped back.

“I – I don’t think it is either, Dean, but you have to admit – ” Sam started before Dean couldn’t stand to hear any more. 

“That’s definitely not the case, Sam, just – just drop it!” He growled before hanging up.

Then he put his head in his hands. That was dumb, now Sam was going to be all suspicious, but…he just couldn’t handle the tiny hope Sam was starting to give him. He wasn’t going to fall for it again, dammit; dating male friends led to nothing but trouble, and adding Cas’ asexuality into the mix was not going to help. 

*~*

So, to stay strong, Dean cancelled pop culture night. Just for one week, just to give himself a chance to breathe and practice being away from Cas (a state he was sure he was going to get awfully familiar with soon enough). He didn’t even have to come up with a way to distract himself that night; Charlie helpfully offered to meet him for a one-on-one session to discuss his D&D character leveling up at the same time as Dean would usually have been meeting Cas. She even split a George’s splurge with him (despite her weird insistence on cheese rather than her usual crazy toppings combo).

...Her insistence made sense when Dean found himself locked in a room with Castiel, he of the picky tastebuds. At first Dean thought Cas was in on it, but Cas was quick to defend himself and Dean had to admit, it wouldn’t be the first time Charlie had gone rogue and betrayed him. (Probably wouldn’t be the last either, if Dean was being honest with himself. Which he wasn’t, at the moment, so he could shove that thought aside for another day.)

Dean bought himself some time by serving up the pizza, but even George’s couldn’t save him for too long; Cas was far too determined to talk. 

…Determined to the point of ultimatums, apparently.

Dean would admit that his first reaction of deflection was…not his finest moment. But…he didn’t know what else to do. He couldn’t lose Cas. But he also couldn’t talk about this, not without shattering Cas’ perception of him completely. Somehow, his earlier confessions hadn’t scared Cas away, but Dean was almost certain any more would be the end of their friendship. 

…How was he supposed to tell Cas that?

How was he supposed to tell Cas that he wasn’t good enough for Cas to date, that Cas was going to find someone better and forget all about Dean soon? That all of this was just Dean preparing for that inevitable future?

He couldn’t.

…But maybe he could tell someone else. If he could just pretend that Cas wasn’t in the room long enough to tell someone else over the phone…

Dean pulled out his phone and dialed Sammy.

“Dean?”

“Heya Sammy. I…I need to tell Cas something.”

Sam groaned. “Yeah, Dean, I know. Why are you talking to me instead of Cas about it?”

“I – Sammy, I don’t know if I can actually say this to Cas’ face. You’re – you’re my test run, okay?”

Sam was quiet for a second. “Okay. Okay, Dean, hit me.”

“Um. The idea of Cas dating is…terrifying. Because I know that whoever Cas decides to date is going to be amazing, so much better than I could ever be, and…I don’t want to get in the way of Cas finding that person, I really don’t. I’m okay with being left behind – ” 

Dean heard Cas make a sound behind him and made a slashing motion in his general direction; if he didn’t get this out now, he never would.

“ – I am. It’s okay – ” 

“But is it?” Sam suddenly interrupted.

“…What?”

“Are you sure that you’re actually okay with being left behind, Dean?”

“I…wh-why wouldn’t I?” Dean stuttered.

“Because you like him as more than a friend, Dean,” Sam replied in his duh-Dean voice.

Dean flushed bright red. “I – why are you saying shit like that, Sam?” he finally blustered in reply after a moment of silence.

“Dean. You’re my big brother. You’re not the only one who can tell when their brother likes someone. Well – I did need a little help, but it’s pretty obvious now. That’s why you’re backing off and hiding it behind the dating excuse; you’re trying to pull away before Cas breaks your heart like Lee did.”

Dean just spluttered incoherently, with no idea how to respond to that.

He snapped out of it when Cas took his phone out of his unresisting hand. “Hi Sam, this is Cas. Yes, I’ve been here the whole time, but I couldn’t hear your side, so – ” 

Dean turned away as Cas went silent. His little brother was probably spilling his guts (and Dean’s. Mostly Dean’s, in fact) and the little shit was going to pay later.

“…Thank you, Sam, that was very enlightening,” Cas finally said. “I think Dean and I need to speak further. Thank you for your help.” And with that, Cas must have hung up, because suddenly, he was standing right next to Dean. 

“…Dean? Can we talk now? Please?”

Dean didn’t respond, but he did plop down on the floor next to where Cas was standing, and didn’t move when Cas slowly sat down.

“Right. Okay. I think we’ve been viewing the past few days very differently,” Cas started carefully.

Dean snorted. 

Cas frowned at him. “I’m serious, Dean. Do you…do you have feelings for me?”

Dean clutched at his hair. “I don’t – I don’t know Cas! You’re hot, you’re fun to be around, I – I want you in my life, but…it’s not like I have any idea what it’s like to actually like a guy, I mean – look how badly I fucked up being with Lee!”

“…You still consider how things ended with Lee to be…your fault?” Cas responded slowly.

“Of course!” Dean snapped. “I’m the fuck-up, I’m the reason people leave or – or I push them away, it’s…it’s always my fault, and I don’t want to do that to you, Cas, but I don’t know how to not!”

Dean felt Cas (gently, so gently) cup his face and turn it to face his grave expression. “Dean Winchester. Based on what you have told me about the situation with…with Lee,” Cas paused before spitting out the name and then barreled on, “absolutely *none* of that was your fault. He was the only one who was at fault. He took advantage of you in your grief and disappeared without any warning, breaking your heart and destroying the progress you had made – Dean. You cannot possibly think that his leaving was your fault.”

Dean closed his eyes. He couldn’t respond, because the only answer he had was the one Cas didn’t want to hear. 

…But as he suspected, his silence was enough of an answer for Cas, as he felt Cas’ hands leave his face. This was it, this was going to be the moment Cas finally – 

…Hugged him? Dean was being hugged within an inch of his life, Cas digging his forehead into Dean’s shoulder. “If I ever meet the person who convinced you that you are not one of the most brilliant, kind and thoughtful people I have ever met, I am going to eviscerate them,” Cas growled.

Dean…didn’t reply, deciding to just bury his face in Cas’ neck instead and enjoy the warm fuzzy feeling Cas’ arms and words were giving him.

Finally he worked up the courage to admit, “I…I would hate to lose…whatever we have when you decide to date someone,” Dean whispered. 

Cas hummed. “First of all, Dean, I would never abandon our friendship because of a dating partner – what is the saying, bros before hos?”

Dean chuckled wetly. “That may be the weirdest thing I’ve ever heard you say.”

“Nevertheless, it is true. You’re important to me, Dean. And secondly, as much as this may come as a surprise to you, I think that you are a very worthy candidate for dating…if you’re comfortable with that.”

Dean shot upright. “I – but – are…are you sure?” he stuttered.

Cas sat up slowly, keeping steady eye contact. “Dean. I am serious. This…while the idea is new to me, I would be honored to be someone you decided to date. You already know that I am asexual, and I know that can be a…problem, for some people. So – you should take some time to think about it. But either way you decide, I’m your friend first and foremost. Okay?”

Dean just nodded, head spinning. This…this was not how he had expected the night to go. He had a lot to think about. But…he had to admit, it felt really good to hear that Cas wanted to date him.


	9. Cas IV

Cas expected everything to change after his dating proposition, but everything was…surprisingly normal. Well, a new normal. Aside from reinstating movie night and starting to eat lunch together again, Dean started joining Cas’ study sessions. Sometimes he had his own studying to do, sometimes he helped Cas by offering a willing ear or a flashcard partner, but even when Dean had no real reason to be there…he was. Just for Cas’ company. It put a warm and cozy feeling in Cas’ chest – and Cas let himself hope. 

*~*

Dean’s roommate spent most of his time in his girlfriend’s room, so usually their pop culture nights were in Dean’s room, but tonight Cas’ roommate was going out to a party, so Cas offered to host for the night. Dean quickly agreed – Cas’ father had insisted on getting Cas a nicer mattress than the school offered, not to mention a nice headboard. Cas was embarrassed at the lengths his father had gone to, but enjoyed getting to share in the luxury with Dean.

And so started their first movie night since their conversation. Cas wasn’t sure what to expect, but The Aristocats certainly wasn’t it. 

“…That accent is *very* French,” Cas commented as the opening song played.

“I know, it’s a little over-the-top, but it was the 70s – and you have to admit it’s catchy.” 

Cas nodded in agreement before refocusing on the adorable kittens playing behind the credits. Dean smirked to himself; he knew Cas would love this movie. 

As the movie entered its climax, the cats finally home in Paris only to be confronted by the greedy butler at the last minute, Cas was starting to get agitated, grumbling insults at the horrible man.

When he captured the cats and put them in a hole-less trunk, Cas couldn’t help himself.   
“He does realize they’ll DIE if he does that, right?” Cas burst out angrily. 

Dean just patted him on the shoulder and pointed at the screen. 

Cas grumbled at him but kept watching. In the end, the butler was the one sentenced to die in a hole-less trunk (poetic and justified, in Cas’ opinion), O’Malley was adopted into the adorable family…and Madame apparently decided to offer her house up as a home to all the alleycats of Paris. “As strange as that is, it’s probably a good use of her wealth and space, not to mention appeasing her loneliness at the same time,” Cas mused out loud. 

Dean just rolled his eyes. “It’s a Disney movie, Cas, you don’t have to think too hard about it. But I do like that all the cats get a home at the end, I always liked that part.”

Cas smiled back. Dean could protest all he wanted, but he was definitely a soft touch under all that bluster. 

*~*

After the movie ended, Dean seemed to have something on his mind – but he just kept fidgeting, not actually saying anything but clearly not wanting Cas to leave yet either. After almost five minutes of this, Cas threw up his hands exasperatedly. “Just say it, Dean.”

Dean stopped fidgeting and squared his shoulders. “I – the D&D group is meeting tomorrow and I think you should come,” he blurted out.

Cas raised an eyebrow. “Dean, you know the only reason I went last time – ” 

“ – was to talk to me, I know. But – I really enjoyed you being there. Not even just because you brought the best snacks, but…” Dean just shrugged. “I’d really appreciate it.”

And after hearing that, how could Cas not go?

*~* 

So he bought all the same snacks he had purchased last time, as they had gone over well, and walked over to the meeting room with Dean. He knew Charlie was happy he was coming, as he had checked in with her to make absolutely sure he was welcome, but he was *not* expecting the rest of the group’s enthusiastic welcome. This time they all introduced themselves – Gabriel was the group’s bard as well as the group’s comedic relief, always cracking jokes and eating his body weight in sugar; Kevin played a cleric, often healing the other characters’ injuries and serving as the voice of reason in opposition to Gabriel’s chaos; Dorothy played a ranger whose fantastic luck when rolling her bow attacks made her character quite the sharpshooter. “She’s definitely cheating, I just haven’t figured out how yet,” Dean groused.

“Just because you can’t roll as well as I can doesn’t mean I’m cheating,” Dorothy shot back with a smirk.

“Alright, alright,” Charlie called. “Don’t be jealous of Dorothy’s skillz with the dice, Dean, it’s not a good look,” Charlie chided, leaving Dean sputtering.

Cas noticed that Dorothy winked at Charlie behind Dean’s back, and Charlie had to clear her throat before fiddling with something behind the screen she had set up. 

Cas smiled to himself, pretending he hadn’t seen anything, as he unpacked the snacks, thanked everyone, and wished them a good session.

To which Charlie cackled, “Define good!” and the rest of the group groaned but quickly settled in. As Cas made to go sit away from the table – away from all the rowdiness, observing from a distance – Dean touched his arm lightly. “Do you want to try watching from here?” Dean asked quietly, gesturing to the seat next to him, still empty despite the closely clustered group. 

Cas hesitated for a moment before slowly sitting down. Charlie winked at him before diving into their adventure.

*~*

Cas had to admit that D&D was far more fun up close rather than observing from afar. Next to Dean, Cas understood the holding-your-breath tension of specific dice rolls, the important distinction between player and character knowledge, the thrill of triumphantly winning a long battle or solving a frustrating puzzle, the hilarious shenanigans certain players enacted and got others sucked into, the delight of stumping Charlie with certain choices; the simple pleasure of watching a story develop and unfold in real time. 

Cas could see why D&D could become such an addicting game. In fact, it was one he was suddenly itching to join himself. After the session wrapped up, Charlie sidled up to Cas. “I have a strict rule against new players joining mid-campaign. But there will definitely be a seat for you next time, if you’re interested?” Charlie asked.

Cas smiled. “I would appreciate that very much, thank you.”

He ignored the subsequent grins and high-five that Dean and Charlie exchanged.

*~*

And for a few more weeks, nothing changed – Cas and Dean continued to spend most of their time together, due to Dean’s sudden availability.

Cas had thought about asking Sam about it, but for now, he was enjoying it too much. He left Sam in the dark, afraid that Sam might say something to his brother and bring it all crashing down around him. 

Not that he and Sam didn’t talk about Dean, but Cas acted like they were back to their original normal, with not much having changed other than Cas starting to attend D&D sessions – nothing about Dean’s new attendance of his study sessions or hanging out in his room after their pop culture nights came to a close. Cas just didn’t want anything to change.

So he was surprised when Dean suddenly brought up visiting his house again over break.

“Any special reason?” Cas asked absently, finishing up the (decaffeinated, it was far too late for anything else) tea he was making them after yet another Disney movie – Moana, this time, and Cas had to admit it was definitely one of his favorites.

Dean cleared his throat awkwardly. “Yeah. Yeah, I – uh…I think it’s time the family met you as – you know. My boyfriend.”

Cas whirled around to face Dean, mouth gaping. 

Dean just rubbed a hand through his hair and shrugged, clearly trying to play it off as no big deal. “Yeah, Cas, we’ve been practically dating for – for a while now, and…it’s time to make it official, doncha think?”

Cas put down the mugs of tea and bowled Dean over in a hug. 

Dean hugged him back, laughing, “Alright, alright!” He sat them both back up far too quickly for Cas’ taste, small frown on his face. “But speaking of – well, dating, I want…I want to make sure I know where your boundaries are.”

Cas just cocked his head at him.

Dean flushed a little but forged on. “Like…hugging is clearly okay. But – kissing? Hanging out less-than-fully-clothed? Holding hands in public? I mean…I just…” He took a deep breath. “I really, really want to do this right, and not do anything that makes you uncomfortable, so…we should talk about that. Sooner rather than later.”

Cas thought about it. “Definitely okay on holding hands in public,” he started. “Hanging out in fewer clothes – as long as all genitalia are out of sight, I should be okay, and I would love to try it…” He paused. “I…would like to try cuddling, probably fully-clothed at first but I am willing to negotiate going forward after that.” 

He wrinkled his nose. “Not so sure about kissing, especially if any tongue is involved, but I can try closed-mouth kisses to start and see what happens. Honestly Dean, I’m not entirely sure, since I’ve never really tried any of this, it’s hard to know what will be good and what will be bad.”

Dean just tugged Cas into a side hug and tucked Cas’ head into his shoulder. “Guess we’ll have to experiment, see what you like and don’t like. But you have to promise you’ll be honest and clear with me, alright? None of this faking it to make me happy bullshit.”

Cas beamed up at him, so glad that Dean Winchester was such an amazing person and grateful that he was lucky enough to call him his boyfriend. “I promise.”


	10. Dean IV

Dean had decided that, in order to seriously think about Cas’ desire to date him, it was important to spend dating-levels of time with him. Which, based on previous dating experience was basically…most of the day, every day. 

This was something that, even during the heights of his infatuation with Lee, had always felt…a bit burdensome, more like a chore than anything. Dean had a little brother to worry about, and his dates weren’t always the best conversational partners, especially when that topic came up.

But with Cas…Dean was surprised to find himself always wanting to spend *more* time with Cas, not less. Cas was equally as interested to talk about Sam as Dean was, and outside of that, had an uncanny intuition for when Dean needed someone to listen, to distract him or to leave him alone. 

So Dean found himself spending more and more time with Cas, to the point that he decided that crashing Cas’ study sessions and starting movie nights back up wasn’t enough – Cas should start coming to D&D regularly.

He was thinking about it as they watched The Aristocats, Cas predictably enchanted with it. Dean had to admit he probably spent more time watching Cas than the movie itself, but…he *had* seen the movie a million times, since it was one of Sam’s favorites growing up. He knew the whole thing backwards and forwards, but through Cas’ eyes, he could almost be watching a whole new movie. 

Once the happy ending was settled and the credits started to roll, Dean knew it was now or never. D&D was meeting tomorrow – if he wanted Cas there, he had to say something tonight or he’d have to wait until the next session. 

And yet his chickenshit mouth refused to say anything, spewing out any other subject aside from the one he actually wanted to discuss. Eventually Cas (the angel) asked what was on his mind. With the direct prompting, Dean was finally able to ask – and somewhat surprisingly, Cas said yes. (Maybe the whole letting-his-feelings-show thing was part of it, and maybe it was something he should do more often, like Sam kept telling him. Maybe.)

And like Dean had thought, it was great to have Cas at D&D. He was definitely a convert, too, if the excitement in his eyes as the session progressed was any indication. Charlie and Dean’s sneaky plan to get Cas into D&D to secretly extend his friend group, because Cas was awesome and deserved more friends, was progressing very well. 

*~*

Eventually, Dean had to admit that he and Cas had basically been dating for a number of months (minus any sexual component that Dean had during previous dating experiences) and Dean was still excited to spend time with Cas every day. It was a great sign that their relationship would be better than any of the ones that came before, and it was time that Dean took the hint and answered Cas’ question that he had been waiting months for. 

It was time to make it official, put a label on it.

But before he could, he had to think long and hard about what he wanted to do about his family. He knew that Sammy and Bobby both knew and would probably be ecstatic that he was dating Cas – they would welcome the news with either excited hugs (Sam) or gruff congratulations (Bobby). 

…His mother, though.

He was almost certain she had no idea her older son wasn’t completely straight, and he wasn’t so sure how she’d react to the news that Dean was definitely not. Taking Cas home to his mom as his boyfriend would be…a huge step. One that he couldn’t come back from. And if his mom reacted badly…he was stuck dealing with the fallout all break. Although, he and Cas could always escape to Bobby’s for the remainder of their time off, should everything end badly. Not that it would, but…Dean couldn’t help worrying.

But if anyone deserved that kind of grand gesture, it was Cas. No matter what his mom might think or say, Cas was important enough to him that he refused to hide it from his family. No matter how she reacted, Cas was worth just about anything. So telling her, and the rest of the family, it was. 

*~*

But first, he had to talk to Cas. And not just asking him about the upcoming trip back to his house. He had to know Cas’ boundaries, so he never accidentally crossed a line or otherwise made Cas uncomfortable; that was the very last thing Dean wanted to do, so they had to talk about it.

...Not that Cas’ responses were quite as clear-cut as Dean had hoped, but they were still good to know. Cas did seem to have a few things he was certain about – handholding and cuddling seemed to be at the top of his list, as long as clothing was on; the rest he wasn’t as sure about, but like Dean said: as long as Cas was open and honest about his feelings and desires, they would find out what Cas liked together – and only at the pace Cas set. 

*~*

As the day of his trip home with Cas came closer and closer, Dean felt himself growing increasingly nervous. So instead of letting himself get psyched out and claim that something had happened at home so they couldn’t go (because he knew Cas would be disappointed but understanding and Dean would drown in his guilt), he called Sammy. 

“Hey Dean, what’s up?” Sammy asked distractedly when he picked up the phone.

Dean took a deep breath. “I’m-bringing-Cas-home-to-introduce-him-as-my-boyfriend-over-break-next-week-and-I’m-so-freaking-nervous,” he blurted out. 

There was a moment of silence as Sam processed the news and then – Dean winced and pulled his phone away from his ear at the high-pitched sounds the kid was making. “Jeez, Samantha, my ears,” Dean muttered bitingly, even as a broad grin stretched over his face. 

“I *knew* Cas was hiding something!” Sam yelped triumphantly, before going quiet. “But Dean, Cas is – Cas is so happy, even if he wouldn’t tell me why; I can tell. And I know *you’re* pretty happy too, otherwise you’d never even think about doing this, so…Dean, what are you so nervous about?”

“M-Mom,” Dean finally gulped. 

“…Oh,” Sam whispered.

“I mean, it’s not like I know for sure what she’ll say, maybe it’ll be absolutely fine…” Dean trailed off. 

“…But what if?” Sam finished for him. “Yeah. Okay, totally fair. Um. Do you want me to test her out first, maybe make some subtle hints – ” 

“No,” Dean yelped, “no-no-no, please don’t. Just…maybe talk to Bobby? And be prepared for it – you know, happening?”

“Totally, Dean, I can do that. In fact, I’m going over to Bobby’s tonight – Mom wants the house Y-chromosome-free for Bunco night,” Sam grumbled. 

Dean could picture the exact face his brother was making and couldn’t help chuckling. “Perfect. You talk to Bobby, and I’ll talk to Cas, and – hopefully – everything’ll go fine. Thanks, Sammy.”

“What’re little brothers for?” Sammy replied with a shit-eating grin so potent Dean swore he could hear it through the phone. “Hey, wait, don’t – ” Sam hung up. “…say anything weird to Bobby,” Dean finished weakly. Sam probably wouldn’t do or say anything too bad…or at least that was the lie Dean was sticking with until he could question (and properly punish) Sam in person.

*~*

As it turned out, while Sam had almost certainly kept his end of the bargain, Dean had procrastinated and procrastinated on warning Cas until they were in the car and already on their way to the Winchester house. It was bad enough that he was giving Cas so little notice, Dean thought wildly, but no heads up at all was just cruel. He had to tell him. NOW. 

“Cas,” Dean blurted out. “I – uh – just so you know…Bobby and Sam already know that I’m bi and that we’re dating, but. I’m not sure how my mom’s going to react – like, I hope it’ll be fine, but…uh. You should know, going in, and…I probably should have warned you sooner,” Dean mumbled, staring fixedly out the windshield. 

Cas patted him gently on the shoulder. “Thank you Dean, for telling me. I appreciate it – and now, Sam owes me lunch,” Cas finished with a smugly satisfied voice. 

Dean just blinked as he tried to process that. 

“So, you two – freaking – Sam bet against me telling you??” Dean finally spluttered. 

“To be fair, he bet you wouldn’t say anything before we were parked at your house. I knew you would end up saying something before that,” Cas explained smugly. 

“That little bitch!” Dean growled. 

After a second, Cas responded, “Sam says you’re a jerk.” And with that, Dean was off, insulting everything from Sam’s taste in music to his getting-way-too-long-hair and his bad-news-friends (not Cas, of course, never Cas) and Dean was so busy being outraged and coming up with insults that he forgot to be nervous. 

*~*

He definitely remembered when they pulled up to park, white-knuckled grip on the steering wheel and hysterically wondering if he should just turn back now, tell everyone he got sick or something – but feeling Cas’ hand squeeze his shoulder reminded Dean that this wasn’t just for him. This was also for Cas, who didn’t deserve to be a secret, who didn’t need another reason to feel any shame about who he was; and that’s what really snapped Dean out of it. He could do this. For Cas.


	11. Bobby I

Bobby knew Sam was coming over that night, since Mary was having one of her girl’s night things and she always asked Bobby if he’d be willing to take her boy(s). After years of saying yes to Mary’s questioning phone calls, Bobby had taken to just grunting “You know I will” into the phone after seeing her name on the caller ID. (That habit had committed him to a number of other unpleasant things over the years, but having the boys over was always worth it.)

In any case, he hadn’t seen Sam so excited to come over in – well, too many years. (He should’ve known better than to think it was over getting to spend some time in his company.) Sam burst through the door and barely gave Bobby a second to say hello before shouting one of the last things Bobby had expected to hear: “Dean and Cas are getting married!”

Bobby spit out the mouthful of water he had been drinking. “What in the blazes – ” 

“Well,” Sam interrupted, still looking far too gleeful for Bobby’s comfort, “Technically that’s an exaggeration. But – ” (Sam continued over Bobby’s groaned, “Dammit, boy.”) “ – Dean is bringing Cas home as his boyfriend and planning to say so to Mom, so…they are pretty serious.”

Bobby did raise an eyebrow at that. Dean had always been so careful in front of him and Mary, like he thought they were expecting him to fit a certain mold. Bobby didn’t care, of course – his boys were just his boys, nothing they could say or do could ever change that. But Mary…Bobby wasn’t too sure how Mary would react. She had always wanted her boys happy but…Mary was far more concerned about the status quo and the opinions of other people in general than the rest of her family (although she was certainly where Dean got his own unhealthy dependence on the opinions of others, in Bobby’s mind). So he could see her deciding to prioritize her son’s current happiness above all…or worry about his future enough that she might try to change it. 

Bobby snapped out of that train of thought as Sam frowned at him. “And Dean doesn’t want me – or you, probably – trying to hint at anything to Mom, see what she might think beforehand.” Bobby chuckled – Sam was good at a lot of things, but subtlety of any kind was a long way down on the list; of course Dean didn’t want Sam blundering into that thorny conversation like the awkward, gangly baby moose he was. Whether Bobby should stick his nose into it or not was a very different matter – *he* knew how to subtly change Mary’s train of thought (the boys had begged him to change their mom’s mind on enough things both big and small over the years, and Bobby had become quite adept at it) but he wouldn’t, if Sam said so. 

*~*

And Bobby had to admit, when Dean walked through that door with Cas’ hand in his, determined glare on his face even as his other hand trembled a little bit, Bobby knew he would do anything and everything for him – up to and including cutting Mary out of his life. ...His own life, and Dean’s, if it came to that. He hoped it wouldn’t, that Mary would see sense, but he was prepared for the worst possible outcome.

Just then, Mary walked by the entryway. Bobby tried to step in front of the boys – block her view, since he knew that Dean was not expecting to face Mary this quickly – but it was too late. 

“Dean – and Cas! Welcome, what brings you by?” Mary asked cheerfully. “Bobby, out of the way, I need to hug my boys!”

Bobby saw Dean’s slight nod out of the corner of his eye, so he stepped out of Mary’s way, turning to watch what happened next. She ran right up to the boys, only paused for a slight frown at their clasped hands before throwing her arms around both of them. “But seriously, what brings you both down here?”

“I, uh…” Dean gulped but his determined expression was back. “I wanted to tell you something.”

“Yes?” Mary asked, pulling back enough to meet Dean’s eyes. 

Dean stood up a little straighter. “I – I know you’ve already met Cas, but. This time I wanted you to meet him as – as my boyfriend.”

“Oh.” Mary replied blankly before hugging the boys again. “That’s – really great, kids, I’m happy for you!” She then stepped back. “This means a celebration! Let me head into town and get something nice, the fridge is pretty much empty here,” she laughed into the sudden awkward tension. Dean and Cas took that as their cue to escape further into the house.

Bobby, however, stayed and watched as Mary grabbed her coat and purse. “You want any company?” He asked as she rushed toward the door. She stopped, took a deep breath. “I – I have a lot to think about,” she sighed. “And since you don’t seem nearly as surprised as I am, I would have appreciated a heads-up, Bobby Singer!” she growled.

Bobby just shrugged. “Sam said Dean asked him not to get involved, I figured the same applied to me. When you’re ready to talk this out with me, you know my number.” And with that, he ambled back into the house, heading for the kitchen. He knew Dean would have headed there first – friendliest and warmest room in the house, not to mention where all the food was – and he had a surrogate son to reassure. Mary saying that she needed to think was a good sign; Bobby had a good feeling about what was going to happen next, even if Dean was going to be worrying himself sick about it.


	12. Mary I

After the second screaming match with John that had included him raising a hand to strike her… even if the blow was never delivered, even if John swore that he would never hurt her, twice was enough of a pattern that it became a threat that Mary decided to heed. She was going to take care of herself and her sons. 

Unfortunately, the boys were old enough to have strong opinions of their own – and they did not want to move to South Dakota with their mother. They wanted to stay at the same schools, keep their same friends and their same rooms in the same house.

And as much as it hurt to separate from her boys, Mary knew she needed to get away from John. So she moved to South Dakota by herself. At least John had agreed to the boys spending their summers with her.

*~*

Mary had decided on Sioux Falls, South Dakota for her new home due to the presence of one Bobby Singer. Bobby and John used to be friends, it was how he and Mary had met, but the two quickly formed a closer bond than John and Bobby had ever had – even after Bobby and John had an epic falling out and lost touch, Mary quietly stayed in contact.

Once John was out of her life, Bobby became an invaluable presence helping her deal with the aftermath of John and the sudden loss of her two boys. He had been there through it all, helped get the boys excited to come up to Sioux Falls every summer, and Mary couldn’t have been more grateful for it.

Of all the times Bobby had had her back, this one time that he didn’t had left Mary reeling. Dean…wasn’t who she thought he was. Her boy had a boyfriend, not a girlfriend. And not just any boyfriend, but Castiel. The poor boy she had welcomed into her family like a son…was now dating her actual son.

Although…that actually…almost…made it better? At least she already knew Cas, knew that this was a kind and thoughtful boy who needed a family and enough kind words to start erasing all the cruel ones he had been absorbing for far too long; this was not the kind of boy who would break her son’s heart. She might need to worry about the other way around, but it certainly could have been worse.

As for Dean not being as interested in girls as she thought…well. He definitely had been in high school, so maybe this was just some sort of college experimentation phase? 

…But Dean was not one to introduce a significant other to family lightly; Mary had only known about all the girls through the town’s grapevine, not from Dean himself. If Dean was going through all the effort of introducing Cas as his boyfriend to the family, this was a serious relationship, not an experiment or a fling.

In which case, Mary needed to get over this and accept it as the new normal sooner rather than later; she was not losing her boys over something so silly as her own ingrained prejudice – she was better than that, and it was time for her to step up and act like it. 

…Actually getting something in town to celebrate would probably be a good start.

*~*

Of course she got to the store and was immediately struck by the fact that she didn’t know what Cas liked to eat! What if she got something he wouldn’t even like, or was allergic to, or – 

She pulled out her phone to call the house when she saw she had a text from Bobby: ‘Castiel’s not allergic to anything and the boy will do just about anything for a good burger. That plus some potatoes for fries, sweet or regular – and maybe some ice cream for homemade milkshakes? Can’t go wrong with chocolate.’

Mary teared up a little at the text. Once again, Bobby Singer had come through for her exactly when she needed him to – so she followed his suggestion, getting ingredients for burgers, fries and milkshakes, as well as some top shelf bourbon from the liquor store next door. Bobby deserved it.

As she headed back to her house, knowing that all her boys were waiting to greet her and share a meal, Mary couldn’t help smiling. Dean had found someone who made him happy, and she was overjoyed that he decided to share his happiness with her and that she could show her support and love for him no matter what – now, now she was really ready to celebrate.


	13. Cas V

Cas knew that both Dean and Sam were worried about Mary and her rushing out the door so fast; but he could also tell that Bobby was quite calm about it, which soothed most of his own fears. 

In the meantime, Cas was happy to participate in whatever method of distraction Dean and Sam preferred as they waited for Mary’s return. He was surprised when the choice was a board game he had never heard of.

“How do you play...” Cas squinted at the box. “Par-cheese-i?”

Sam chuckled as Dean just stared uncomprehendingly. “It’s pronounced Par-cheesy, Cas, and the rules aren’t too complicated – ”

“Okay, a childhood without Disney movies is cruel enough, but – no Parcheesi? Did you play *any* board games growing up?” Dean interrupted. 

Cas paused as he thought. “The only one I can think of had a bunch of colored squares and fake money...and something to do with business?”

Dean and Sam groaned in unison, “Not Monopoly...”

Cas brightened at that. “Oh yes, that’s it!”

“Nope, nope, I refuse to let that awful game be your only board game experience, sit,” Dean ordered. “Bobby, you playing?”

“No, I’m fine just watching,” Bobby smirked as he pulled up a chair. “And watch out for Dean, he cheats.”

“That is a lie, I can’t help it if I roll really well,” Dean retorted as he set up the board – red in front of Sammy, blue in front of him, and yellow in front of Cas. Sam started to explain the rules, but pretty soon Cas started frowning in confusion. 

“Sammy, stop for a sec,” Dean groaned as he gestured as Cas’ expression.

“What’s up, Cas, am I going too fast?” Sam asked.

“No, I think I get the rules so far,” Cas started, frowning a little bit. “What I am confused about is why you keep referring to your pieces as people and sending them back home as…murder?”

Dean and Sam looked at each other and shrugged. “I don’t know who started it, it’s just – something that happened.”

Bobby grunted. “I taught them how to play, and I definitely didn’t explain it that way, but next thing I know, these two idjits have started talking like that, and…” Bobby shrugged. “You get used to it.”

Cas raised an eyebrow but let it go. Sam finished his explanation of the rules, Cas nodding along.

“Anything we forgot, Bobby?” Dean asked as Sam started shaking the dice in his hand.

“Not that I can think of, have at it boys,” was Bobby’s smirked reply.

Dean ended up winning the first game, although Sam certainly put up a fight, but then Cas started rolling almost spookily perfect numbers, racking up win after win as Dean got more and more frustrated and Sam more and more gleeful.

After Cas’ fifth win in a row, Dean threw up his hands. “Cas must have weighted the dice somehow!” he growled as Sam burst out laughing. 

“Serves you right, you wanted Cas to play, and now he’s broken your oh-so-great winning streak – Cas, you are more than welcome to play anytime. Anytime,” Sam smirked. 

Bobby chuckled in the background as Dean let out a groan. “I should have known you’d team up with Sammy against me,” he grumbled. 

Cas was about to suggest the three of them try some other game when he heard the front door open. 

“Hey boys, I’m home – and I got the stuff for Bobby’s burgers!”

Both Winchester boys lit up and ran out of the kitchen, leaving Cas to stare quizzically at Bobby. “Your burgers?”

Bobby just winked at him. “I’ve got a secret recipe, makes ‘em better than anything you can get in a restaurant. You’ll see.”

Dean and Sam came crashing back in, arms loaded with groceries, with Mary close on their heels. 

“Figured burgers, fries and milkshakes would be a pretty great celebration dinner,” she explained happily as she went over to Cas’ chair and gave him a hug. 

Cas hugged her back, tears prickling at his eyes. “I…yes, that sounds wonderful,” he replied after clearing his throat. 

Mary smiled down at him. “Wish I could take all the credit, but it was Bobby’s idea.”

Cas turned to thank Bobby, but the gruff man just held up a hand. “It’s not a big deal, please don’t get all worked up about it,” he grumped. “If you really want to thank me, you can help me make them.”

Cas nodded just as Dean barreled up to Bobby. “I’ve been trying to get you to tell me the recipe for YEARS and Cas gets to know after just a couple days??” Dean exclaimed.

“Yep,” Bobby replied casually. “Now shoo, you and Sam go – play cards, or something, but get out of my kitchen. Don’t let him peek, Samuel!” he called sternly as Sam raced out of the kitchen, Dean sulkily following. 

“Promise,” Sam called back.

“Alright boy, to start – do not get the already-made patties. The trick is hand-shaping them yourself…”

*~*

After the burgers were ready, Bobby made Cas swear not to tell Dean anything Bobby had taught him. “It’s a secret Dean has tried too many underhanded ways to get, so he’s lost any right to get it honestly. Do not fall for any of his tricks,” Bobby explained sternly. “And this way, if he really wants a taste of home while he’s at school, you can make them for him. But don’t let him watch while you’re making them – get a friend to distract him or something, because he will try to sneak in the kitchen to take a look, I’ve caught him far too many times.”

Cas nods solemnly. “I promise.”

After everyone was seated and served, Cas groaned happily into the first bite of his burger. “These make me very happy,” he couldn’t help moaning, ignoring Dean’s blush and smiling at Bobby’s subtle preening. After Cas had demolished his burger and was left with only a few fries to pick at, Dean immediately started in on the whining and bargaining Bobby had warned him about, but Cas stood firm.

“You wouldn’t want me to disappoint Bobby, would you Dean?” Cas finally said.

Dean paused, mouth open, as Sam cackled next to him. “He’s got you there, Dean!” Sam chortled.

Dean pouted, but brightened when Cas promised to make them to the best of his ability in the dorm kitchen at a later date.

*~*

After stuffing themselves at dinner, Cas offered to help clean up but Mary shooed him out of the kitchen with Sam and Dean. The three boys started to watch Captain America: The First Avenger. Cas had never seen the Marvel movies, and Sam finally convinced Dean that if they were only watching one movie, to ease Cas into the whole saga, this was the best move. Full, cozied up next to Dean (his boyfriend!) on the couch and watching an amazing movie about the power of a “little guy” – Cas was overwhelmed with how happy he felt, in this moment. He was so, so lucky.

After the movie ended (sadly, Cas admitted, but Dean soothed his worries by promising that Cap found more equilibrium over the next couple movies), Sam yawned and headed off to bed; Dean started to do the same, dragging Cas to the stairs along with him, until Mary poked her head out of the kitchen. “You boys better not get up to anything up there,” she warned, “I don’t want to be hearing anything tonight. Neither do Bobby and Sam.”

Cas just tilted his head confusedly as Dean blushed. “I promise, Mom, nothing’s going to happen, can we please go now?”

Mary waved a hand amusedly as Dean scampered up the stairs, Cas towed along behind him. 

“I’m sorry about her,” Dean winced as they entered his room. “She wouldn’t bother if she knew, but…I didn’t want to out you without talking about it first.”

Cas flushed as he realized what Mary had been implying. “Oh.”

Dean rubbed the back of his neck. “Yeah. Sorry, again. Um. Do you want first shower, or…?”

“No, go ahead,” Cas replied quickly.

“Okay, but – don’t go snooping, okay?” Dean instructed sternly as he headed back out into the hallway. 

“Promise,” Cas chuckled as he started to unpack his travel bag. He did look around at all the posters and knick-knacks around the room while Dean was occupied – of course Dean had a vast collection, some featuring characters or images he recognized, but many of them still unfamiliar to him. There was a poster that had the now-familiar Captain America along with a number of other characters; Cas figured he would be introduced to them in subsequent Marvel movies. 

Cas was so absorbed with what was on Dean’s walls, he forgot to check for what was on Dean’s floor; he missed the rather large tripping hazard of Dean’s luggage and ended up sprawled on Dean’s carpet.

“Everything okay in there?” Sam called from what sounded to be a couple rooms away.

“All good, I just tripped,” Cas called back. From this vantage point, there was something Cas could almost see, hidden at an awkward angle under the bed…

He wiggled closer, hands outstretched, until his fingers went from barely brushing the object to firmly grasping it and dragging it out. It was a box, a white one, that sounded full of…something when he shook it, but still had very little weight.

Cas was about to push it back under the bed – it wasn’t his business what Dean stored there, and he could always ask about it later – when Dean came barging in, hair still wet and a thick towel wrapped loosely around his hips.

“Cas, I heard – ” Dean stopped dead in his tracks before throwing himself down next to Cas, ripping the box out of his hands and shoving it hastily under the bed. “Nope.”

Cas just opened his mouth, to reassure Dean that he was about to put it back, but Dean continued talking. “Not talking about that, Cas. Period.”

…Well, Cas hadn’t been all that interested in knowing, but now that it was so firmly denied he was burning with curiosity. But he could bide his time until tomorrow, when he could ask Sam. For now, he was willing to let Dean put an end to that conversation.

He mulled over what it could possibly be while in the shower – porn magazines, perhaps? That would explain the rustling sound and some of Dean’s reaction, but not all of it, nor the lack of weight. Nothing else really occurred to Cas, though, so he focused on getting out of the shower and getting ready for bed instead. 

Seemingly to apologize for his earlier abrupt manner, Dean had arranged for them to watch The Princess Bride on his laptop. “This is a classic, Cas, and deserves your full attention,” Dean firmly instructed him before pressing play.

And Cas had to admit, it was a fantastic movie. He chuckled at all the jokes, gasped at the dramatic reveals, sighed at the romantic moments…it was the perfect movie to get his mind off of Dean’s mystery.

He was tired enough to drift off almost immediately after getting under the covers, no stressing or worrying about sharing a bed with Dean for the first time like he had feared.

*~*

The next morning, while Dean was occupied helping Bobby make bacon (“the most important breakfast food, Cas!”), Cas sidled up to Sam. 

“Any chance you know what’s in the box under Dean’s bed?”

“Under Dean’s bed…?” Sam muttered to himself before groaning and burying his head in his hands. “Nope, nope I can’t,” he moaned before pulling out his phone and texting Dean, presumably.

Dean was a little occupied with the bacon when his phone buzzed, but after he saw it, Cas noticed that Dean flushed a bright red. Interesting. Maybe Sam’s text would convince Dean to talk about whatever he was hiding; they were boyfriends now, after all.


	14. Dean V

Dean was terrified that his mother was going to go on her shopping trip and come back only to tell him that he was a disgrace and no longer welcome in her house. 

Sam and Bobby could tell that Dean was panicking, but then Bobby had the brilliant suggestion of pulling out Parcheesi – a game that Dean and Sam had hundreds of hours of fond memories from playing. 

Dean was horrified that his boyfriend had not only never heard of Parcheesi, but had only ever played Monopoly before. It was time for Cas to get *educated.*

Unfortunately, Cas got a little too educated – he started winning game after game, and Dean got…a little frustrated, admittedly. Parcheesi was supposed to be *his* game, dammit!

But he was not left to stew for long; his mom came in laden with groceries pretty soon after Cas’ fifth win. Dean and Sam both raced over to help her; Sam took the lion’s share of the bags as Dean got an extra-long hug and a whispered reminder that she loved him, no matter what. Dean squeezed her back before taking a fairer share of the grocery bags and running back into the kitchen to unpack them.

Dean was putting his groceries away when he heard Bobby offer to teach Cas how to make his secret burgers – and *what*??

“I’ve been trying to get you to tell me the recipe for YEARS and Cas gets to know after just a few days??” Dean exclaimed.

Instead of understanding the level of cruelty he had stooped to, Bobby just agreed with Dean and banished him from the kitchen, ordered Sam to keep him busy. Like he was a damn dog.

Dean sulked his way to the living room, Sam smirking as he brandished a deck of cards. “Bet you can’t beat me at Gin,” Sam taunted.

“Oh, you’re on, bitch,” Dean retorted, cracking his knuckles.

“We’ll see, jerk,” his brother smirked as he dealt the cards. 

Dean was so focused on crushing his (cheating) little brother into the ground that he didn’t give Cas knowing the secret burger recipe another thought until they were actually sitting down to eat. Then he continued to hold in his indignation until Cas had mostly finished eating; after which Dean started his interrogation. 

“So, Cas…I already know that Bobby never starts with pre-made patties, he hand-shapes them.”

Cas didn’t respond.

Dean frowned. “Come on, I already know it, confirming it doesn’t change anything.”

Cas stayed silent.

“Fine,” Dean grumbled, “be that way. You’re a horrible boyfriend.”

No response. Dean stayed quiet for about a minute before bursting out, “Seriously?? Nothing??”

Cas turned to face him and gave a single nod.

Dean growled and threw his hands up; his boyfriend was a monster.

He did try a couple more (less dignified) tactics as the milkshakes came to the table and were slowly sucked down, but eventually Cas shut him up: “You wouldn’t want me to disappoint Bobby would you, Dean?”

Sammy, the little shit, thought that was the funniest thing he had ever heard. 

Dean decided to retreat into sullen silence with what was left of his dignity.

*~*

After dinner, Sammy suggested watching Captain America: The First Avenger. It was one of Dean’s favorite Marvel movies, and Cas hadn’t seen it; two birds, one stone. Dean had to admit his brother knew how to cheer him up; it was a very good movie, and Cas got really into it, which was always fun for Dean to watch. Cas was definitely a Cap fan – probably because the two had a similar moral code, Dean realized as he chuckled to himself. 

Sam and Cas both turned to look at him, as his chuckle had come at a rather dramatic moment. “Just a funny thought, guys, keep watching,” Dean quickly explained, so the other two turned back to the screen. Cas took the opportunity to snuggle a little bit closer to Dean, and Dean felt incandescently happy. His family knew about Cas and nothing had changed; nothing, absolutely nothing was going to ruin this night.

*~*

Dean was a little worried about Mary’s unnecessary warning, but Cas barely even noticed it, so Dean wasn’t going to let it bother him either. He warned Cas not to snoop around his room while he got in the shower and enjoyed the far greater water pressure than anything campus had to offer.

While he was a little worried about sharing a bed with Cas, by the time he got out of the shower he had mostly calmed down; of course, when he got to his room, Cas had somehow found his box of…Lee’s gifts. 

Dean immediately yanked them out of Cas’ hands and shoved them hastily back under the bed. “Nope.”

When Cas opened his mouth, Dean’s stomach roiled and he snapped, “Not talking about that, Cas. Period.”

After that nasty surprise, Dean was all worked up again. He tried to calm himself down while Cas was in the shower, but he was too agitated to concentrate on much – so he decided that he and Cas should watch one of his comfort movies, yet another one that Cas hadn’t seen yet: The Princess Bride. 

Dean felt the tension start to leave his body as the familiar bedroom came on screen. He focused on watching the movie and enjoying Cas’ reactions; he knew Cas would love this movie, and he was so glad he got to share it with him. 

By the end of the movie, Cas was barely awake and Dean put everything away as Cas crawled under the covers and immediately passed out. Dean chuckled to himself; guess he was worried for no reason. He drifted off to sleep pretty quickly himself after that.

*~*

The next morning, Dean woke up first. He carefully got up and got dressed, tiptoeing down the hall to the bathroom. He hadn’t beat Sam, unfortunately, who always took way too long dealing with his L’Oreal mop, so Dean knocked hard on the door to let Sam know he was waiting and sat down in the hallway.

Last night…definitely could have gone worse, Dean admitted to himself, but he had not expected Cas to find his panty collection. That was not something Dean had expected to deal with so soon – and he knew Cas. Just because his boyfriend had been distracted by The Princess Bride and his own fatigue did not mean that Cas was going to let Dean’s immediate shutdown of the topic go. Dean was going to get badgered for information, sooner rather than later, and he had better have a plan when it happened.

But first, Dean smirked as the bathroom door opened and Sam flounced out – all offended that his hair routine had been interrupted, the brat – first, he was going to forget about it and enjoy his morning. Bobby was probably starting breakfast by now, maybe Dean could convince him to let him make bacon. Bobby and Cas couldn’t get all the cooking glory.

*~*

Dean didn’t see when Sam or Cas entered the kitchen, too engrossed in the bacon he was cooking. At some point he definitely felt his phone buzz in his pocket, but he wasn’t sure exactly when and didn’t check it until he sat down at the table. 

When he did, he saw he had a text from Sam: ‘Cas just asked me about the box you have under your bed. I have a strong suspicion about what’s inside, please please please do not make me explain to YOUR BOYFRIEND about your…collection. Please.’

Dean immediately flushed bright red. Dammit. Sam was right, he shouldn’t have to explain what was in the box, but…a small part of him thought this all would be so much easier if Sam had spilled the beans. But nope, Dean was going to have to find the words to explain to his boyfriend that he had a box of girl’s underwear from his…ex-whatever-Lee-was under his bed. Fantastic.

*~*

Based on the curious glances from Cas and the insistent staring from Sam over lunch, Dean’s avoidance tactics were not going to hold up for very long – especially with Bobby and Mary catching on to both Sam and Cas trying to get Dean’s attention, and shooting him some questioning looks of their own.

Dean scarfed his lunch in record time and asked to be excused, running straight to his room and locking the door behind him before pulling the box back out from under his bed. 

He didn’t know how long he was sitting there staring at it, but he was interrupted when someone knocked on his door and Bobby’s familiar gruff voice asked if everything was alright.

Dean sighed. “Yeah, Bobby, but – can you send Cas up?”

“Sure, kid. Gonna unlock the door for him?”

“Yup.”

“Okay,” Bobby replied before Dean heard him thump back downstairs. 

Dean stared at the box in his hands, starting to sweat a little, and jumped when he heard Cas’ knock. “Dean?”

“Cas,” Dean responded croakily before clearing his throat. “Gimme a sec,” he continued as he placed the box down (carefully) and got up to unlock the door. He opened it to let Cas in, but quickly closed and locked it again. He saw Cas zero in on the box before focusing on Dean’s face. 

His expression must have been worse than he expected, because Cas immediately looked worried. “Dean? Are you okay?”

Dean scrubbed a hand through his hair. “I – um. I think so. Mostly. Uh. This…this is not a great topic.”

Cas’ face immediately fell. “Dean, I didn’t – ”

“No,” Dean interrupted, “don’t feel bad. It’s not – I should tell you, now. I probably shouldn’t have buried it for so long as it is.” He went quiet for a minute. “I, uh. You remember Lee?”

Cas’ face could have been carved out of stone. “Yes, I remember,” he gritted out.

“Right. Well, I may have left out…a significant aspect of our…thing,” Dean hedged. “This box is what’s left of it.”

Cas’ brow furrowed. “What’s left of what?”

Dean just kept rambling. “I know, I should have just gotten rid of them, but – I don’t know, it was something I liked before he decided to get his assholery all over it, and – one day, I thought, one day I’d regret it, so – ” He gestured at the box. “Here they are.”

“Dean,” Cas asked patiently, “here what are?”

Dean flushed a light pink. “I, uh…guess I never said, huh. Or really mentioned it at all, otherwise. Um. Shit. Well, let me start off by saying that just because I like it doesn’t mean you’re in any way obligated to like it too, it’s not like I haven’t put it aside for a couple years at this point anyway, so – just, don’t pretend for me, okay? Promise?”

Cas blinked at him. “I genuinely have no idea what you’re talking about, Dean, but I promise that nothing you have to say is going to change my opinion of you.”

Dean huffed out a breath. “There’s a first time for everything.”

And before Cas could say anything, he just took the top of the box off.


	15. Cas VI

Underwear. 

That’s what was in Dean’s box.

And not just underwear. Colorful, silky, expensive-looking women’s underwear.

Panties.

There was a lot of black, red and pink, along with a sprinkling of other colors, but Cas couldn’t help noticing that one pair…one pair was a shade of blue almost exactly the same as his eyes.

He immediately wondered what it would be like, to see Dean wearing underwear the color of his eyes – and the mental image caused a wave of heat to sweep through him. That…that would be a sight. 

Cas was yanked out of his surprising train of thought by Dean’s tremulous “…Cas?”

Immediately he ripped his eyes away from the box and focused on Dean’s worried face.

“You…wore these? For Lee?” Cas asked carefully.

Dean squirmed. “Well, I mean, I…I liked to before Lee, but…” He waved a hand at the box. “These are all the ones he got for me.”

Cas frowned. “All these?”

Dean bit his lip. “Yeah, at the time I didn’t really think about it, but it was weird that he could keep getting his hands on so many…” He stiffened. “I hope he didn’t steal them.”

“I’m sure he didn’t,” Cas tried to console, rubbing a hand up and down Dean’s arm. He wasn’t as sure as he was trying to sound, but no point in upsetting Dean. Maybe he could distract him…

So Cas did what he had been longing to do since he saw them – he picked up the almost-perfect blue panties, fingering the silky material. “These are very nice, Dean,” he rumbled, voice having gone surprisingly deep all of a sudden. 

He heard Dean’s embarrassed cough, but kept his eyes on the prize in his hands.

“I think they’d look even better on you,” he continued, looking up to see Dean’s flush deepen to more of a scarlet shade.

“I – you can’t – you can’t just say stuff like that, Cas!” Dean squeaked.

Cas tilted his head. “Why not?”

Dean started to sputter something incoherent in answer but was interrupted by Bobby calling them down to dinner. Dean quickly stood up, yanked the panties out of Cas’ hands and shoved them in the box and the box under the bed before dragging Cas downstairs.

Cas went without protest. He had a lot to think about, and a lot of time to figure out what to do with the information that had fallen in his lap.

…And he definitely wanted to do something with it.

*~*

Both Dean and Cas were distracted during dinner, but even with all the thoughts whirling in his head, Cas noticed that Sam was uncharacteristically quiet. 

After dinner, while Dean was helping Bobby and Mary clean up, Cas pulled Sam aside. “Is everything okay?” he whispered.

Sam looked back toward the kitchen before gesturing upstairs. The two ended up in Sam’s room, door closed. 

“I just…” Sam sighed. “It’s really nice that you and Dean don’t have to hide your relationship, that Dean doesn’t have to hide who he is. And I guess…I’m wondering if it’s time for me to do the same.”

Cas stayed silent, sensing that Sam still had more to say.

Sam turned to face him. “I mean, Bobby and Mom took Dean’s coming out pretty well, right? And, I know being ace is different, but…I shouldn’t be so scared after that…”

Cas placed a comforting hand on his shoulder. “Coming out is scary, especially to people you love and are afraid to lose. They don’t know about me, either – and the idea of telling them is…frightening,” Cas admitted. “Maybe…maybe I could come out to them first, see how they react?” he mused.

Sam shook his head firmly. “No way. No, I don’t want you doing that for me.” He sighed. “I want to, but maybe…telling them is going to mean telling them *everything,* including that Dean lied, so we should definitely talk to him before we do anything.”

Cas nodded. “And maybe he’ll have some ideas we haven’t thought of because we’re a little too close to it?”

“True,” Sam agreed. “We won’t do anything until we talk to Dean.”

So, together, they waited to hear Dean’s tread on the stairs. Once they did, they both peeked out and beckoned for Dean to join them. “You guys okay?” Dean immediately asked, noticing the worry on their faces.

Cas turned to Sam, who took a deep breath. “I…I think it’s time I came out to Mom and Bobby,” he confessed.

Dean rubbed a hand over his mouth. “Okay…so what’s the plan?”

Cas sighed. “We don’t really have one?”

Dean pursed his lips as he thought. “First of all – do not tell them together. Better to tell Bobby first. He took me being bi really well, and he helped Mom get used to it too; same tactic should work for you. Secondly, if you are going to ambush Bobby, have some materials ready for him to read – he’s going to want to do some research, better to have some good resources prepped ahead of time. Thirdly…how much telling are we talking here? Cas being ace, too?”

Cas bit his lip. “I think so. Which will mean coming clean about your original…exaggeration, as well.”

Dean waved a hand. “I’m not worried about that, Bobby will get it and I bet Mom won’t even notice. But Cas – are you sure?”

Cas straightened his shoulders. “If Sam’s doing it, I should too – no need for any of us to hide.”

Dean blew out a breath. “Alright. Like I said, Bobby first. But before that, research.”

*~*

Sam and Cas put their research skills to work the next day, while Dean played interference with Bobby and Mary. Aside from giving some excuse for their absentmindedness and disappearances aside from meals, the two boys weren’t fussed about the details and focused on gathering a variety of useful and well-written materials.

By the evening, after dinner, they were ready. They were going to talk to Bobby, together, the next chance they could.

…Meaning the next chance Dean created. He went grocery shopping with Mary that afternoon, claiming that she wasn’t getting enough snacks for movie night – or was it the right snacks? In any case, he got Mary out of the house and promised to text them at the start of the return trip.

It wasn’t hard to find Bobby, after Mary left. He was sitting in the kitchen, reading a book.

He looked up as they entered and shut it, sighing. “Knew getting some peace and quiet in this house was too good to be true. Well?”

Sam opened his mouth, but nothing came out.

Cas glanced at him and stepped slightly forward. “Sam and I…wanted to talk to you. About…something important.”

Bobby turned to face them properly. “Yes?”

Sam started fidgeting as Cas stepped back. “I…well. You know how you already knew that Dean wasn’t. You know.”

Bobby raised an eyebrow. “If you mean that I knew he wasn’t 100% straight, then yes.”

“Right. Um. I – I don’t think I’m 100% straight either,” Sam started quietly.

Bobby stayed silent.

“I – um. This should not be this hard,” Sam whispered to himself before straightening his shoulders. “Okay. Dean is bi, because he’s attracted to multiple genders. Straight, gay and lesbian people are attracted to one gender. But…there’s also people who aren’t attracted to anyone.”

“Ah,” Bobby sat back slightly in his seat. “I see.”

Sam cleared his throat. “Yeah. And uh, I’m – I’m someone in the last category. I’m not attracted to people – ” 

“Asexual or aromantic?” was Bobby’s unexpected interruption. 

“Wh-what?” Sam stuttered, glancing back at Cas. They hadn’t planned for this.

“Boy, you think after I learned about Dean, that I didn’t do my research? There’s all sorts in this world, and just knowing about a few of them is no way to go through life. I may not know everything, but I know what not being attracted to people means. So – asexual or aromantic?”

Sam blinked hard. “Asexual,” he croaked. “Probably heteroromantic.”

Bobby smiled. “Well, thank you for trusting me with this, Sam. You’re still my boy.” And with that he held his arms wide open and Sam ran into them, hugging Bobby within an inch of his life.

Cas smiled at the heartwarming scene. Sam was so lucky to have such a supportive family.

“And you?” Bobby asked gruffly after letting Sam go and subtly wiping at his eyes. “Did you come just to give Sam support, or do you have something to tell me too?”

Cas gulped. “I – I’m ace too. And, actually, that’s how Sam and I met – Dean heard me say I was ace at a GSA meeting, and asked if…well. Asked if I would be willing to talk to his little brother about being ace, basically. Sam and I were friends before Dean and I were.”

Bobby shook his head. “Of course that idjit decided to harass a stranger to help Sam – because he did harass you, didn’t he?”

Cas and Sam both squirmed. “Harass is not *exactly* the word I’d use…” Cas hedged.

Bobby snorted. “Boy has a one-track mind, has ever since he was little. Sorry that he decided to focus on you – ” 

“Thank you,” Cas interrupted, “but I’m not. Without it, I…I never would have met Sam, or you, or Mary – and I definitely would not be dating Dean. I…you all have been beyond amazing, welcoming me into your home and your hearts, and I…” Cas sniffled. “I wouldn’t change anything for the world.” 

“Don’t get me started again,” Bobby complained, but he and Sam both enclosed Cas in a hug. 

Sam sighed after they all let go. “Now I just need to tell Mom. Any ideas how best to do that, Bobby?”

Bobby nodded. “Yeah, if – if it’s okay with you, let me have a talk with her before you spring it on her? She was not happy about Dean’s talk being out of the blue, and I promised I wouldn’t let that happen again,” Bobby finished apologetically. 

“Yeah,” Sam replied, face brightening. “That’s – good, actually, I didn’t – I don’t – want to…you know.”

“No worries, kid, I gotcha,” Bobby responded gently. “Now why don’t you two skedaddle, I’ll deal with Mary and Dean when they get back.”

So Cas and Sam ran upstairs, texting Dean the all clear and deciding to pass the time until his return playing (and learning, in Cas’ case) some card games.

Sam enjoyed his victories at first, but once Cas learned the rules of each game, he quickly started steamrolling the younger boy. Once Sam grew tired of losing, he would introduce Cas to a new game – and the cycle started again. Sam was starting to run out of new games when he heard his mom and Dean enter the house. 

It wasn’t long after that Dean came crashing in. “Well?” he asked breathlessly.

Sam beamed at him. “It went great! And Bobby said he’d talk to Mom, so I’m waiting to tell her til he gives me the all clear, but – I feel a whole lot better knowing he’s on my side.”

Dean smiled fondly at his little brother. “I bet.” He glanced a little nervously at Cas. “And you?”

Cas smiled back. “Bobby reacted well to my coming out as well; we’re all good.”

Dean’s smile grew even wider. “Great. That’s so great!”

Cas was happy that his and Sam’s coming out to Bobby had gone so well…but now that it was mostly over, he had other conversations on his mind – these ones with Dean, about a certain box underneath his bed.


	16. Dean VI

Dean thought his heart was going to beat out his chest. Cas was just staring into the box, not saying anything, and his face wasn’t moving - Dean couldn’t tell what he was thinking.

Finally he forced out, “…Cas?”

And Cas’ eyes immediately met his.

“You…wore these? For Lee?” Cas asked.

Dean squirmed at the sudden onslaught of memories. “Well, I mean, I…I liked to before Lee, but…” He waved a hand at the box. “These are all the ones he got for me.”

Cas frowned. “All these?”

Dean bit his lip, uncomfortable with the thoughts suddenly occurring to him. “Yeah, at the time I didn’t really think about it, but it was weird that he could keep getting his hands on so many…” He stiffened. “I hope he didn’t steal them.”

“I’m sure he didn’t,” Cas replied in a comforting voice, rubbing a hand up and down Dean’s arm. Dean focused on the soothing sensation, grounding himself in the here and now instead of his memories, and was not doing such a great job – until Cas reached into the box.

“These are very nice, Dean,” Cas suddenly rumbled in a surprisingly low timbre, snapping Dean’s attention to the blue panties he was carefully rubbing between his fingers.

The blue was almost the same color as Cas’ eyes, and Dean felt warm all over as he imagined wearing them for Cas, and he let out an embarrassed cough. 

Then Cas had to keep talking. “I think they’d look even better on you.” 

Dean thought his skin was going to catch fire, his face was so hot. “I – you can’t – you can’t just stay stuff like that, Cas!” Dean responded (not squeaked, of course not). 

Cas tilted his head. “Why not?”

Dean knew he was sputtering some sort of noise, but hell if he knew what it was, too busy imagining how Cas would look at him if he was actually wearing the panties he was still cradling in those large, steady hands…

But Dean was abruptly jerked out of his train of thought when Bobby called them down to dinner. Immediately, Dean yanked the panties out of Cas’ hands, shoved them in the box and the box under his bed and dragged Cas downstairs.

Cas was ace, and Dean was going to stop perving on him in his mind RIGHT. NOW.

*~*

Not that his mind got the memo during dinner, but Dean soldiered on. He decided the best way to shut his brain up on the subject of Cas and panties was helping his mom and Bobby clean up after dinner, which not only worked, but also earned him some brownie points with them – win-win.

He was starting to lose the battle again as he made his way up the stairs, but he was quickly distracted by Cas and Sam’s worried faces peeking out of the door of Sam’s room. Immediately he barged in, and Cas closed the door behind him. “You guys okay?”

Cas didn’t answer, turning to Sammy instead, who took a deep breath, before hesitantly confessing, “I…I think it’s time I came out to Mom and Bobby.”

Dean rubbed a hand over his mouth as he thought. Kid was right, if Dean was out and proud or whatever, it couldn’t be easy to still be hiding. But… “Okay…so what’s the plan?”

Cas sighed that they didn’t really have one. Unusual for both of them to jump in headfirst into a decision like this without having a plan, but these were extenuating circumstances, Dean had to admit. 

Dean pursed his lips. Okay, game plan time. Basically, divide and conquer – get Bobby alone and tell him first, then deal with telling Mom. But before telling Bobby, it was critical to do some groundwork; get the man some material to read and research.

Dean easily settled into planning mode, thoughts of Cas and panties pushed far, far away…for now.

*~*

Dean spent the next day distracting Mom and Bobby from how absent Cas and Sam were as they researched; Bobby was definitely giving him some looks, but let it go, while his mom was more oblivious. Not that it was any sort of chore for Dean to spend time with them; he hadn’t realized how much he had missed their company until he was back home. 

And once Cas and Sam were ready, he asked his mom if he could go grocery shopping with her; he was appalled at the lack of snacks in the house for movie night, and he wanted to do some restocking – clearly his mom couldn’t be trusted. She laughed at his dramatics, but easily agreed.

He spent most of the car ride there chattering about his D&D group and what had been happening to their characters; it was a good group, and there were plenty of hilarious shenanigans to share – especially about Gabriel and his bard character. 

Once they were in the store, the two Winchesters split up – Dean with a basket to collect the all-important snacks, and his mom with a cart to get the rest of the also important but much less exciting groceries. 

Dean made sure to get a pretty equal distribution of his and Sam’s favorites, but realized that he wasn’t sure what Cas’ preferences were. He had brought a good assortment to D&D, but Dean couldn’t remember whether Cas actually ate that much of anything. He didn’t want to buy a whole bunch of things Cas might not even like, so he doubled up on what he knew he and Sam did like – maybe Cas would enjoy some of it too, and if not he and Sam wouldn’t mind.

But it did put a slight damper on his enthusiasm, realizing that even after becoming boyfriends, there was still so much he didn’t know about Cas. 

Which put him right back in the how-would-Cas-feel-about-him-in-panties train of thought. Dammit.

So Dean was a little scowly and maybe – maybe! – he was stomping a little as he met up with his mom.

“Uh oh, what’s got you all worked up?” she asked half-teasingly, half-genuinely.

Dean stewed silently. How to explain this to his mom without getting too…detailed?

Nope. Nothing came to mind. “Nothing,” he grumbled, head hanging.

She was silent for a beat. “Oh, there definitely is. Let me guess – something about Cas?”

Dean immediately faced her head-on, mouth gaping a little. How – 

“I know you think I’m ancient, but I was your age once, Dean. Not to mention psychic mom powers,” she nodded seriously, tapping her temple. 

Dean rolled his eyes; she had been trying to make that a thing for years, but usually it was actually – “What did Bobby tell you?”

Mary put a hand to her chest and gasped theatrically. “I’m wounded! How dare you doubt your incredibly insightful and intelligent mother!”

Dean raised an eyebrow.

“Fine,” she grumbled, “Bobby was worrying about how quickly you and Cas had gotten together a couple nights ago, surprised you boys hadn’t had more issues – said that you were probably due for some soon and I should be keeping an eye out.”

That sounded more like it. “It’s not…it’s not a problem, exactly,” Dean hedged.

“But?”

“But…I guess, there’s still so much I don’t know about Cas. I don’t even know what his snack preferences are! Or his family, or if I’m his first boyfriend, or – well, a lot,” Dean trailed off, blushing as the rest of his thought, “what his kinks are” blared in his brain. Absolutely no way he was saying that in front of his mom.

She hummed in thought as they started walking through the store again. “Well, snack preferences seems like an easy one – just ask him the next time you boys have a movie night. As for the rest…relationships aren’t easy, Dean, and one of the best ways to create a great one is also one of the hardest: you have to communicate, and communicate honestly. I’m guessing that his family is definitely going to be a sore spot, so maybe don’t press too hard about it, but tell him about some of your family history, and your romantic history; show him that you trust him, and you want him to know about you, and if he’s the kinda guy I think he is, he’ll do the same when he’s ready. And if not – well, you just refer him to me or Bobby,” she finished sternly.

Dean nodded slowly, thinking through what his mom had said. “He…already knows a lot about me,” he started slowly, “but…I guess I haven’t asked some of the questions I should. He may not know…that I want to know.”

“Communication is key,” she singsonged.

“Yeah, yeah,” Dean grumbled. “You said that already – any actual tips as to how to make that happen?”

“Nope,” his mom responded cheerfully, “cryptic and/or vague advice only!”

“Can I get a refund then?” Dean deadpanned.

She laughed. “Of course not! But, maybe you want to talk to Bobby at some point?”

“Hmm. That’s actually not a bad idea,” Dean mused. “He’ll be more helpful than you, anyway.”

“Ouch!” She mimed getting stabbed in the chest. “Right in the heart!”

“Alright, alright, stop making a scene in the middle of the store,” Dean grumbled, giving her a quick hug before hustling them to the checkout line.

*~*

In the car on the way home, he sent out a warning text to Sam and Cas, but he didn’t get a response. He figured that it was most likely because they weren’t done with talking to Bobby, and not something ridiculous like the talk with Bobby went so bad that they both turned their phones off. (Sometimes Dean’s brain was a jerk, okay?)

When they arrived at the house, laden with groceries, Bobby was alone in the kitchen. He didn’t seem upset or deep in his own thoughts, so Dean was guessing that everything went well. Good. He got more confirmation when he checked his phone – he had missed a text from Sammy that gave the all-clear for their return, so it had definitely happened, even if Sammy didn’t say how the talk went one way or the other.

He finished putting the groceries away with the two adults, and thought about it. Did he want to talk to Bobby now, or check in with Cas and Sammy first?

No, more important to check in on them. Talking to Bobby could wait. So he ran upstairs and crashed into Sammy’s room when he noticed that the door was closed. “Well?” he asked breathlessly. 

Sammy was happy, and Cas was too after Dean checked in a little more nervously. Good, they were good. Which meant that, even though he felt a little guilty about it, Dean hightailed it back downstairs to talk to Bobby.

His mom must have given Bobby the heads up, because he did not seem surprised by Dean’s nervous, fidgeted request to talk. He just stood up and gestured for Dean to follow him out the garage. Dean immediately calmed down surrounded by the smell of engine oil and metal, in the room that had been his refuge from the outside world for so long. 

Bobby pulled up two chairs and sat himself down. “What’s got you so twisted up, kid?” Bobby asked gruffly but not unkindly.

Dean sat down. “I just…” He fell silent as he tried to get his thoughts in order. “I want…I want Cas to trust me and tell me things now that we’re boyfriends. But – but it was so hard just telling him stuff about Dad and Lee, and I – I don’t want to pressure him, I just…” Dean sighed. “I just want him to know that I’m here when he’s ready to talk,” he finally mumbled.

Bobby leaned back in his chair a little. “Sounds like you two need to have a conversation,” was the unsympathetic reply.

Dean flushed. “I know that! I just – I don’t know how to start it, or – or say what I want to say without scaring him off or hurting his feelings.”

Bobby sighed. “Communication is important, kid, but honesty might be more important – if this has been bothering you, you probably should have this conversation sooner rather than later.” Bobby squinted at him. “And the one about you being sexual while he’s ace would probably be a good one to have, too.”

Dean flushed another couple shades of red. “Bobby!”

“I’m not kidding,” came the unimpressed reply. “Talk it out now and set boundaries before you two rush into something one or both of you are going to regret. Ya hear me?”

“I hear you,” Dean replied, mortified.

“And you might as well start now,” Bobby directed as he stood up. “Gotta start talking to your mom about asexuality, so you all should stay upstairs for now, okay?”

Dean muttered an affirmative and fled.


	17. Cas VII

Almost immediately after arriving, Dean was backing out of the room. “Glad you two are great, just wanted to check in, but I, uh, forgot to ask Bobby something!” And he practically fled out the door, closing it quickly behind him.

Cas turned to blink at Sam. Had that actually just happened? 

Sam looked as confused as Cas. “That…was definitely weird.”

Cas bit his lip. Had he done something? Said something? Maybe – 

“Okay, I can see you working yourself up from here,” Sam interrupted, “and you shouldn’t be. Dean can be weird sometimes, just – let’s play something else.” Sam looked around before lighting up. “Oooh, Boggle! I forgot about Boggle, no one else in the house will play with me anymore – and it’s easy, come on!”

So Cas let himself get pulled into playing Boggle – which was indeed fun, if a little loud between rounds. He was almost completely distracted from Dean’s strange behavior; at least until Dean came knocking, almost timidly, at Sam’s door. “Uh, Sammy is it…is it okay if I borrow Cas for a little while?” Dean asked awkwardly.

Cas barely had the chance to look at Sam before he was shooing the both of them off. “Yes, go! I’ve got other things I can do in here.”

Dean smiled gratefully at his brother. “Thanks. And, uh – Bobby’s talking to Mom, so maybe…y’know. Stay up here and out of the way for now?”

Sam nodded. “Got it.”

Dean met Cas’ gaze for only a second before gesturing for Cas to follow him and heading out the door. Cas looked back at Sam, who gave him a thumbs-up and a mouthed, “Good luck,” before following his boyfriend to his room. 

Cas sat down on the bed as Dean paced nervously. “Okay. Okay. This – I have a lot I want to talk about, but – some of it is…a lot, okay? Just give me a chance to try and get it all out without interrupting?”

Cas mimed zipping his lips, starting to worry a little about what Dean was going to say.

Dean nodded firmly. “Okay. So, first things, I know – I know I told you a lot about my…background. A lot of the stuff that’s been messing me up. And you’ve been amazing, really – but. It kinda feels weird to know that you know so much about me and I know…basically nothing about you?”

Cas frowned, and Dean immediately barreled on. “Not that you owe me, that there’s some equivalent exchange thing – I told you mine, now you have to tell me yours – but. I just…I want to know so I don’t hurt you accidentally. I want to help you the way you helped me,” Dean continued almost helplessly. “Just…promise me you’ll think about it?”

Cas nodded slowly. Dean did make some good points. 

Dean blew out a sigh. “Okay, good. Secondly, I think – as boyfriends – while this is kinda sorta something we talked about, both Mom and Bobby made a point of reminding me honesty and communication are the best foundation for a relationship, and – I want us to last. So, they’re important to me; I want you to know you can talk to me, the way I know I can talk to you. About anything. Agreed?”

Cas nodded enthusiastically; this was something he had been meaning to bring up soon, if Dean hadn’t, so to hear it from Dean like this was a huge relief.

Dean’s shoulders relaxed a little. “Good. Good, that’s – great. Um.” Dean flushed. “This one is going to be the hardest, but – you’re gonna need to give me something after I’m done, so just…bear with me for a little longer.” 

Cas raised an eyebrow but nodded.

Dean cleared his throat. “Look. Truth is, you’re ace, and – I’m not. I don’t think I’m going to have problems not having sex, because it’s been a while on that count anyway, but – I just think we should talk about your boundaries, and what…what you’re okay with, and what you’re not.” Dean swallowed. “I’m pretty sure you’re into the whole me-wearing-panties thing, but – to what point? Like, just looking? Touching?” He blushed even harder. “Getting me to come, like Lee? Or is that too much?” Dean gestured broadly. “I just don’t know, and – I don’t want to push for too much, or assume, or – whatever.”

Dean buried his face in his hands. “Please say something and put me out of my misery,” he moaned.

Cas sat and stared as his mind spun with possibilities. Finally, he cleared his throat and Dean’s eyes whipped up to meet his.

“I…I don’t know if I have all the answers you want,” Cas started slowly. “But I’ve always felt that my interest in sex was best described as somewhere between neutral and opposed – or indifferent and repulsed, if you want to use the scale properly. But. The point is – whatever I am, I am definitely interested in looking and touching, that is for certain. As for doing anything like – that asshole,” he spat, “my only interest in doing anything like him is replacing bad memories with better ones.” His voice grew deeper. “So, at least to start, plan on that happening. And depending on how it goes, I am very interested in…exploring further avenues. And Dean? This is not a one-way street. It’s not only up to me, what we do and what’s on the table. I want to know what interests you, what happens in your secret fantasies – and do my best to make them reality.” He coughed lightly. “After doing some research, of course. I don’t – I don’t know for sure what is within my comfort zone, or what my boundaries are exactly, but – I have some ideas. And there’s plenty of room to…investigate.” 

Dean just blinked at him – for a starting-to-be-worrying amount of time – and then his face turned a fiery red. “Cas! I told you, you can’t – you can’t just say stuff like that!” he squawked. 

Cas tilted his head. “And why not?”

Dean threw his hands over his eyes. “Because,” he whined.

“Because?” Cas asked, stepping a little closer to Dean.

Dean stumbled back a step or two. “Because – because! Because I said so!”

“And why do you say so?” Cas asked in his most deadpan voice, grinning wickedly as he continued to follow Dean, until Dean finally hit the wall of his bedroom and had nowhere else to go.

Dean just whined. It took a little while for that whine to become words: “Cas, please.”

“Please what, Dean?” Cas asked slowly, savoring the words and faintly noticing that his voice sounded noticeably deeper.

Dean’s response was delayed (again. Interesting.) but eventually he dropped his hands and peeked up at Cas through his eyelashes. “Please stop – saying stuff! I don’t – ” 

“You don’t what, Dean?” Cas asked calmly. “You don’t like it? Or – perhaps – ” Cas grinned sharply as he looked at the front of Dean’s pants. “Perhaps you like it a bit too much?”

Dean followed Cas’ gaze down and – somehow – his blush got darker. He stuttered some incomprehensible syllables before sliding down the wall until he hit the floor, wrapping his arms around his folded legs and burying his head in his knees. 

Cas stared at his boyfriend, realizing exactly what had been coming out of his mouth and cringed. Slowly, he walked to where Dean was now crouching, and sat down cross-legged. “I’m sorry,” he apologized softly, “I think I may have overstepped a bit.”

Dean peeked up at Cas for a second before burying his head again. “I mean, a little,” came a muffled reply. “But not…not entirely, either.”

Cas smiled briefly (he hadn’t messed this up entirely!) before sobering (he still hadn’t been right to do what he did). “Just because you liked it, Dean, doesn’t mean I didn’t ignore your boundaries and make you uncomfortable without your permission. This sort of thing…” Cas wavered a bit – not sure Dean had ever actually put it together – before continuing. “Safe, sane and consensual is the motto, right?”

Dean shot fully upright, staring at Cas. “That’s – that’s for whips and shit, not for – ” Dean gestured. “Stuff like this.”

Cas raised an eyebrow. “Why not?”

Dean just spluttered.

Cas sighed. “I can’t say I know too much about…a lot of areas concerning sex, but this is something I’ve…looked into,” he hedged. “And if this is the sort of thing that you and Lee engaged in, and you had no idea that rules applied – Dean. You and I both need to look more into what is expected of us and what it entails before going any further. I don’t want to hurt you.”

He gestured at Dean’s defensive position, feeling slightly sick to his stomach. “Look what I’ve done already.”

Dean immediately uncurled, leaning forward. “It wasn’t because of you!”

Cas laughed bitterly.

“No, really!” Dean protested, crawling forward to wrap Cas in a hug. “I – just – I was overwhelmed,” he confessed in a rush as Cas buried his face in Dean’s neck. “You’re right, Lee did – some of this stuff, and – hearing it from you was just stirring up a lot. Lee may have been awful, but he was pretty good at making me feel great, and – just, it was a lot to be feeling all at once, not to mention the whole ace thing and worrying if getting hard would be a compliment or a turn-off on top of it – it was just a bit too much,” he admitted reluctantly. “But it wasn’t your fault, it was mine.”

Cas blew out a sigh, and Dean shivered. “Like I said, we have to do some research.”

“Research, dammit, that’s you and Sammy’s department,” Dean grumbled halfheartedly.

Cas couldn’t help rolling his eyes. “You’re just as good at research, Mr. Encyclopedic Knowledge of Cars and Rock Music, as long as it interests you. And my guess is that research into BDSM will end up being very interesting indeed.”

Dean’s neck got hot, and Cas smiled as he pictured the blush spreading over his boyfriend’s face. “I hate it when you’re right,” Dean groaned. 

Cas’ smile morphed into a smug smirk. “Get used to it,” he teased as he sat up. “And we should get to researching…maybe in different rooms,” he added quietly as he stared at Dean’s full-body stretch. 

Dean smirked. “You sure?”

Cas shook his head rapidly. “Yes, definitely different rooms, you distraction you,” he replied, flapping his hands in Dean’s general direction. “Now shoo.”

“You’re the boss,” Dean winked as he left.

Cas groaned. His boyfriend was going to be the death of him – but what a way to go.

For now, he should get to his research, like he had told Dean.


	18. Dean VII

Bobby was right, as much as Dean hated to admit it. Better to talk to Cas now, get it all out and – well, see what Cas thought about it all. Dean just had to force himself to say everything he wanted to say…and maybe ask Cas not to say anything until he had forced out everything he wanted to say. Yeah.

…If Cas interrupted, Dean wasn’t sure he’d be able to start again. So: he had to talk to Cas. That meant collecting Cas from Sammy’s room. Step one. He could do this.

He knocked on Sammy’s door. “Uh, Sammy, is it – is it okay if I borrow Cas for a little while?”

Cas looked surprised, but Sammy immediately replied in the affirmative, shooing them both off. Dean made sure to warn him about Bobby’s conversation with their mom before leading Cas to his room.

Cas sat down while Dean paced, heart racing. He had to do this, he could – no, he *would* do this. No backing out now. 

After confirming that Cas would stay quiet while Dean got through all the things he wanted to say, Dean decided to start with what he was probably most worried about – asking about Cas’ past. Or, at least, asking Cas to consider trusting Dean with his past, so that Dean could do for Cas what his boyfriend had done for him. Dean felt like it all came out a little jumbled, but at least Cas didn’t seem angry or upset. So point to Dean. 

Cas definitely liked hearing the next bit about honesty and communication, as Dean had assumed he would – it was a bit of a buffer topic, Dean could admit; an easy point to score and put Cas in a good mood for the next part – the one Dean felt shakiest about.

Their sex life, or lack thereof, going forward. Because Dean was not an idiot, Cas was definitely intrigued by his collection. On the other hand, to what degree was…unknown. And Dean didn’t want to assume…

After an unknown amount of word vomit, Dean just buried his face in his hands. “Please say something and put me out of my misery,” he moaned. 

Cas was silent for longer than Dean was expecting, and he almost raised his head to check on his boyfriend when Cas cleared his throat. So Dean immediately met his gaze.

Dean was paying attention to what Cas was saying at first, but once his voice started dipping from its usual rumble to a bit of growl, Dean was – okay, he was distracted, so sue him! He had no idea his boyfriend’s voice could go that low, and then Cas’ pupils started to blow wider, and – it was sending most of Dean’s thoughts into a tailspin. He was only human!

Eventually Cas coughed, his voice returning to a more normal register and his pupils shrinking back, so Dean zoned back in. Cas – Cas didn’t know what his boundaries were? Did…could that mean that Dean was going to be Cas’ first – anything? The mere idea once again crashed Dean’s brain, and he had to reboot before he could say anything else. 

When he was back online, he felt his face get hot. “Cas! I told you, you can’t – you can’t just say stuff like that!”

Cas just tilted his head, the adorable bastard. “And why not?”

Dean threw a hand over his eyes – he couldn’t let himself get distracted again. He was trying to make a point here! “Because!”

“Because?” Cas asked, sounding a little closer.

Dean took a couple steps backwards, a little awkwardly. The more distance he had between him and Cas right now, the better for his focus. “Because – because! Because I said so!” Not that the distance he already had was helping much.

“And why do you say so?” came Cas’ smug reply as Dean felt himself back into a wall. His brain whited out a bit at the realization that Cas had trapped him, and when he could think again, all he could think to say was – “Cas, please.”

“Please what, Dean?” was Cas’ growled reply. 

Growling again, great, that shut Dean up for way too long, but he finally got himself together again long enough to drop his hands and get a look at Cas. “Please stop – saying stuff! I don’t – ”

“You don’t what? You don’t like it? Or – perhaps – ” Dean looked up at Cas’ pause, and noticed Cas wasn’t looking at his face anymore. “Perhaps you like it a little too much?”

What was – No. Dean looked down and yup, he was starting to get hard. Shit. Shit-shit-shit, why would Cas even want to see that, he was ace, Dean had to – 

He wasn’t sure what was coming out of his mouth as he slid down the wall and curled up, hiding from Cas’ view, but he assumed it was as scrambled to Cas as it was to him. In the darkness of his closed eyes, Dean just took the chance to breathe.

He heard Cas slowly walk in front of him and sit down through his breathing.

He was not expecting Cas to apologize – it surprised him enough that his mouth decided to cooperate for once, and he and Cas started to have an actual, normal conversation.

Well, until Cas made the ridiculous connection between what he and Cas had been doing, and – actual shit that needed safewords. Not just talking to each other. Maybe Dean had reacted strongly, but – that was his messed up brain, not anything Cas had done.

Not that Cas saw it that way, so Dean did his best to explain to Cas exactly what had been going on in his brain – which, admittedly, was complicated and layered. It wasn’t all bad, was his point, and Cas seemed to understand a little better after Dean explained (yay for communication). Giving Cas a hug through his explanation might have helped too.

But then Cas insisted on doing research, and Dean grumbled a bit. He hated doing research, he had to do enough of that shit at school, but…as much as he hated to admit it, it was probably important. Cas won this round.

So Dean stretched, making sure Cas got an eyeful as he did so. Cas’ stare was hot and achieved his revenge for making him do research on his break – win-win.

It did get him kicked out of his own room, but it was so worth it. He could procrastinate on his research by going to check in with Sammy.

*~*

But when he got into Sam’s room, he wasn’t there. Dean hung around for a few minutes, waiting for his brother to reappear, but when he didn’t, Dean just sighed and sat down at Sam’s desk. He pulled out his phone and started halfheartedly doing some research, figuring that Sam would show up at some point. But before he knew it, Dean was much farther down the rabbit hole than he had intended, and jumped when Sam suddenly asked from behind him, “What’re you doing?”

“N-nothing,” Dean stuttered, shoving his phone in his pocket. “Where have you been?”

Sam lit up. “Actually, Mom and Bobby and I were just talking – and I did it, I came out to Mom, and it went great!”

Dean smiled and ruffled Sam’s hair. “That’s awesome, Sammy!”

Sammy rolled his eyes as Dean messed with his hair, but he couldn’t stop the grin that took over his face. “Yeah, it really is. Oh, and Mom wanted me to tell Cas that she’s sorry for what she said your first night here, let me go – ” 

Dean threw up an arm to stop him. “Uh. Maybe now is not...the best time?”

Sam stared at him suspiciously. “…Do I want to know why?”

Dean’s gaze wandered as he felt his face heat up. “Um. Almost definitely not.”

“Gotcha,” Sam replied, sounding as though he was making one of his milder bitchfaces. It definitely would have been a worse one if he knew, or if Dean had let him go talk to Cas unprepared. 

Searching for anything else to talk about, Dean’s gaze landed on the Boggle game still out on Sam’s bed. “Oh man, you talked Cas into playing Boggle with you?” Dean groaned.

Sam stuck his tongue out at him. “For your information, Cas actually enjoyed playing Boggle!”

Dean rolled his eyes. “Of course he did, the nerd,” he replied fondly.

Sam smirked. “Bet you can’t beat his score.”

Dean scowled. “Oh, you’re on!”

*~*

After a humiliating loss at Boggle (how had he let himself be tricked into playing, again?), Dean slunk back to his room. Cas was still staring avidly at his laptop.

Dean stopped short. “Still…researching?” he asked.

Cas looked up, pensive look on his face. “Indeed. How…much have you gotten done?”

Dean looked away. “Not that much,” he muttered.

Cas sighed and patted the bed next to him. “Come on, then.”

Dean hopped up on the bed and settled next to Cas, peering at the laptop screen.

“Basically – it looks like you have submissive tendencies, and I’ve got dominant ones. And everyone seems to have different ideas of what that means…” Cas paused. “Which sounds like we get to decide what it means to us.”

Dean glanced at Cas. “Sounds like a plan to me.”

Cas smiled. “Perfect. I did look into some of these…activities. I think both of us are okay with putting aside any kind of penetration, at least for the moment, yes?” 

Dean nodded.

Cas took a deep breath. “So. Like I said before, this is not only about me. If there’s something you’re interested in that I haven’t thought of, or something I’ve thought of that makes you uncomfortable, you have to tell me.”

“Right,” Dean replied a little breathlessly, licking his lips.

Cas cleared his throat. “Right. So. Obviously, we’re both interested in your wearing panties – I figured I’d use that as a bit of a starting point, and see what else people with…similar interests also like.”

Dean’s brain started to fuzz out a little at all the possibilities Cas was parading in front of him. He spoke up when something didn’t sound all that appealing or really bothered him, but as a whole…Cas had found some very, very good ideas.

At some point, Dean grabbed Cas’ hand. Theirs may have been an unconventional relationship - in more ways than one - but they were forging their own path. Together. And Dean was so grateful for every minute they were going to spend walking it hand-in-hand.

**Notes for the Chapter:**

> And that's a wrap! Hope you enjoyed :)
> 
> As I mentioned, there will be a sequel coming next month - this fic was mostly dealing with Dean's family issues; next time, it's Cas' turn!


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